I feel like he's making a fool out of me.

October 14, 2012 6:13 AM

I think my boyfriend is hitting on his best friend's (adult) daughter. I am hurt and angry and upset and I don't know what I should do.

For simplicity's sake, I will refer to boyfriend as SO, boyfriend's best friend as BF, and boyfriend's best friend's daughter as D.

In case it's relavant, my SO is about 15 years older than me. I'm in my late 20s. We have been together 4 years, but do not cohabitate.

My SO's best friend BF has a daughter D who is a pre-med student at NYU. SO doesn't see BF very often. Recently BF was in town for his D's 21st birthday, and SO used this as an opportunity to hang out with BF for a while. He ended up crashing with BF and D in D's small off-campus apartment for the night.

Next day SO is telling me how he feels he has grown apart from BF a bit (they've been friends since high school). BF's wife passed away last year and BF now has a trashy trophy girlfriend who is very annoying and wasn't much fun to hang out with. SO said that D has turned out to be a pretty cool kid, very smart, pre-med, and he ended up talking with her through most of the evening rather than deal with BF's new trashy girlfriend. SO accidentally left his jacket at D's apartment. This was about 3 weeks ago.

Last night we were out late watching the Yankee game at our favorite bar, and on the train on the way home I saw him texting. He thought I was asleep I guess, but I was reading over his shoulder (yes, quasi snooping I guess, not so great). Turns out he has D's phone number now, and had texted her earlier in the night complaining about how cold he is. My eyesight is pretty good, so I could read most of the conversation. This is what I saw:

SO to D: Damn cold outside, wish I had my jacket.
D to SO: oh dear, I hope you at least have a scarf.
SO to D: Naked through the streets of NYC. Hope u can sleep 2night.
D to SO: drama queen
SO to D: maybe a little bit. stayed out late watching the yankee game. a little drunk.

I don't know if D texted back or not after that. I was furious and upset (and a little drunk). I pulled away from SO and tried to keep from crying. I did not tell him what I'd seen or how I was feeling. SO realized I was awake and started trying to crack jokes and make me smile, but I was really upset. I told him that I was just exhausted - not the best move to lie, I know, but I didn't know how to bring up what I'd just seen since it was quasi-snooping. I went home and spent most of the night crying.

My questions are:

1. I think those texts were kind of flirtatious. I know that the hive mind does not know my SO or D (and I have never met D), but I was just curious to get some outside opinions as to whether the texts were flirtatious or if I am just imagining things.

2. If they do seem flirtatious, what should I do? Do I bring it up with him? How?

3. I am feeling hurt and betrayed right now. I love this man - he makes me laugh and he's changed my life for the good in many ways. Some of my friends expressed reservations when we first started dating because he is so much older than me and not very conventionally attractive - they said I could do better and I was squandering my youth on some guy's mid-life crisis. I ignored those hurtful comments at the time because I find him wildly attractive and charismatic and I didn't think I was his mid-life crisis. I didn't care what it looked like from the outside - just how I felt about him and how he felt about me. Now I feel like the rug has been pulled from beneath me and my friends were right - I've squandered my youth on this older guy and now he's moving on to a girl younger than me and making a fool out of me.

Then again maybe it's just a harmless little crush - I get those sometimes too and they're kind of fun but I don't act on them. And maybe it's not fair to not allow him the same. But I don't send flirtatious texts to my crushes that way - I think that's a line that shouldn't be crossed.

I also am thinking about myself at age 21 (D's age) and how I would feel if my father's best friend started sending me drunk flirty texts - I'd have been grossed out. (I still would be grossed out.) So maybe this will resolve itself soon enough - she'll tell him to back off, or she'll tell her dad and her dad will have it out with SO.

But I don't know what I should do RIGHT NOW, if anything. I'm hurting, my heart is hurting, and I feel like a fool. I suffer from depression and I've fallen into a hole since last night and can't seem to break out of it. I want to know if I am overreacting - am I? - or if this is actually a big enough deal that I should start thinking about DTMFA-ing.

Please help, hive mind. I am crying right now writing this out and I feel out of control and helpless and angry and hurt and I don't know what to do. Any thoughts, advice, kind words, tough love, anything will do. I just need some perspective. Help.

posted by anonymous to Human Relations (65 answers total)

I don't know if D texted back or not after that. I was furious and upset (and a little drunk). I pulled away from SO and tried to keep from crying. I did not tell him what I'd seen or how I was feeling. SO realized I was awake and started trying to crack jokes and make me smile, but I was really upset. I told him that I was just exhausted - not the best move to lie, I know, but I didn't know how to bring up what I'd just seen since it was quasi-snooping. I went home and spent most of the night crying.

The main problem is that you didn't tell him what you were upset about. Problems can't be addressed if you keep the reasons for your feelings a secret.
posted by xingcat at 6:19 AM on October 14, 2012 [17 favorites]

"Okay, so yeah, I saw you texting D last night and it seemed kinda flirty to me and it bothered me a lot more than I thought it would."

Those words, to him, as soon as you can find a quiet and secluded place to say them. The longer you go without saying what the problem is, the harder it is going to be to get it out in the open.
posted by Mooski at 6:25 AM on October 14, 2012 [20 favorites]

Talk to your SO. "Was that D you were texting with on the train last night? I thought I was just upset since I was a little drunk but I'm still upset about it today so I want to talk about it. What's going on?"
posted by headnsouth at 6:28 AM on October 14, 2012 [13 favorites]

Yes, talk to him. If this is a one-off-- mentioning D three weeks ago, and then this texting business-- it could mean absolutely nothing. Especially in the context of four years. By now you probably have some idea if he is generally flirtatious or a player or always likes to have someone on the back burner. (People I've dated who turned out to be like that usually showed their hands pretty quickly. It's not even that these were bad people; that was just their relationship style and you had to take or leave it.)

If there is anything else-- like, has he had "mentionitis" about D in the three weeks since meeting her? have you had similar experiences with him that you didn't like in the past?-- it may be that you're just going to realize you can't accept the way he's acting in general. In that case, before talking to him, you should decide what the goals of any conversation will be. Nothing is worse than going into a conversation with a strong feeling you already don't trust the person and that you're probably going to hear something you don't like. But if it's the text episode alone, it's not worth assuming anything.
posted by BibiRose at 6:44 AM on October 14, 2012 [1 favorite]

I definitely think asking him about it and telling him the content of the messages made you uncomfortable is the next step. I'll chime in as requested and say I think it's weird for your SO to be messaging this woman and telling her how drunk he is and taking about his nakedness. That does seem a little flirty. Be prepared for him to be defensive about it- I imagine he'll be embarrassed about the whole thing either way. Don't let him shame you into feeling bad for being suspicious. If he gets too upset, tell him you'll give him some more time to think about it and you can talk again later. Just like it probably wouldn't have gone well when you were drunk, it's not going to go well if he's feeling vulnerable and resorts to the knee-jerk reactions.
posted by ThePinkSuperhero at 6:47 AM on October 14, 2012 [4 favorites]

Yes, they are flirty. Not a lot but enough. Shifty. I agree with the scripts others have written above. You can and should still address this. It's going to eat at you otherwise. Remember: you're not a fool, you're just looking out for the relationship. It's a bad move your boyfriend is making. A serious mistake. His buddy won't take kindly to this flirtation either. And maybe, for your guy, this puts her in the safe zone, a person who he cannot date because his buddy would kill him and he's in a relationship. But, it's not cool and she's not the person he wants to flirt with. Bad idea all around. Talk to him; don't kick your relationship to the curb before you have it out.
posted by amanda at 6:57 AM on October 14, 2012

I wanted to offer a possibly different perspective. I agree that the text seem borderline flirty, but only borderline. However, another way of looking at it is that he may be trying to just relate to D. It's his friend's daughter and he may just be feeling out how to relate to her in an adult way. I definitely have seen this lead to awkwardness when the motives of people were not in doubt (e.g. straight older male trying to relate to the son of one of his friends).

As others have said, though, the only way to start to know is to talk to him. However, if something relatively small like this can send you reeling off ("I'm hurting, my heart is hurting, and I feel like a fool."), maybe your spidey sense is telling you this relationship is not in not in a great state?
posted by Betelgeuse at 7:08 AM on October 14, 2012 [1 favorite]

I agree the texts are flirty -- not so much blatantly flirtatious as sending the message "I want to flirt with you." If I had received these texts, the gratuitous mentions of nakedness (not having a coat =/= naked) + drunkenness (setting the stage for the later step-back "oh sorry, I was a little drunk last night") would send me a pretty clear signal. If I wasn't interested in the guy, this feeling would be strong enough that I'd purposely text back something referencing him as pal or buddy or friend.
posted by sallybrown at 7:11 AM on October 14, 2012 [10 favorites]

Sneaky texting (when he thinks you're asleep) is a Big Red Flag. When you talk to him, don't come at it from an accusatory frame of mind, but also be on the lookout for defensive over reactions. Defensive over reactions to a completely reasonable expression of your concern and feelings (with the mea culpa of admitting the snooping) would be Big Red Flag number two.

Other things - like BibiRose's "mentionitis" (excellent term!) or changes in your sex life are smaller, but not insignificant Red Flags.


I've mentioned in past AskMe's that I used to be a serial cheater, and have gained from that a ridiculous suspicion of people to be involved in cheating, so maybe I'm over sensitive, BUT so far, I'm not often wrong. People act squirrely in dozens of ways when they're emotionally and physically moving away from you, and YOU will likely feel it before you realize you are feeling it.
posted by nile_red at 7:47 AM on October 14, 2012 [9 favorites]

Whatever happens here, I think you would benefit from getting out of the mindset that you've "squandered your youth". You're not less of a person than you were five years ago. In fact, I suspect you're a better person! You're probably more mature, more relaxed, more rounded, and more knowledgable. The mid-twenties are prime growing time.

If your relationship ends (and we don't know it will), there'll be guys who want to date you no matter what your age. Promise.
posted by Georgina at 7:49 AM on October 14, 2012 [15 favorites]

I want to know if I am overreacting - am I? - or if this is actually a big enough deal that I should start thinking about DTMFA-ing.

Yes, you're overreacting. It's one text, that you haven't talked with him about and yet you're thinking about dumping him. That seems a bit dramatic.

You're talking to the wrong people. None of our opinions matter, none of us know you or him.

Talk with your guy, see what's going on.
posted by Brandon Blatcher at 7:53 AM on October 14, 2012 [11 favorites]

I have never met D

Remedy this, stat.

Basically, I think there are two above-board ways this can go.

A) SO retrieves his jacket from D. Single serving friendship complete. The end. Maybe they run into each other again down the line, are cordial like adults are.

B) You guys collectively become friends with D.

Anything else is bad news bears.

I probably would have said, "oooh, who are you texting?" when I noticed what was up. But I'd rather be openly nosy than borderline snoopish. The fact that you continued to snoop but didn't just come out and ask in the moment is a much bigger red flag to me than what's going on between him and this kid.
posted by Sara C. at 7:54 AM on October 14, 2012 [5 favorites]

FWIW, I would have written something similar, entirely innocently.

Though in fairness, my friends do call me a bit of a flirt (perhaps because I would have written something like that and thought nothing of it).

Short answer - Ask him about it.
posted by pla at 8:14 AM on October 14, 2012 [1 favorite]

I don't know if D texted back or not after that. I was furious and upset (and a little drunk). I pulled away from SO and tried to keep from crying.

I... have no idea why. This is borderline, arguably, possibly flirty but just as likely to be totally innocent and you are driving directly to the worst assumption in floods of tears. If you want to know the answer to a question, just ask it: "So what's up with you texting BF's daughter?"

I wonder if you're feeling threatened because she's in your age group but even younger. Is you being younger than your SO something you feel is a valuable commodity in your relationship?
posted by DarlingBri at 8:20 AM on October 14, 2012 [19 favorites]

Another approach you could consider taking is to communicate with SO in a way that separates you emotionally from the situation (from his perspective). For example, you could say to him something like "I think you should be careful". And he'll say "About what?". And you could say something like "If you send a lot of text messages to D, D might take it the wrong way and BF might also knee-cap you." That way he'll know that you know what he's doing, and he'll probably also take it that you disapprove, i.e., you are not necessarily accusing him of anything but you are expressing the sentiment that it's at least borderline flirtatious. So the focus of the conversation is about his behavior and how others might interpret it, rather than how you feel about it. That way he can in turn focus on his behavior too, and hopefully change it. Not sure I explained that entirely clearly but anyway just wanted to offer this as an alternative approach for you. Of course if you feel there are general relationship issues that you should take the opportunity to discuss, then you might want to get more into how you feel about it since that can open up many other related topics for discussion.
posted by Dansaman at 9:12 AM on October 14, 2012 [9 favorites]

It's not that the text is exactly flirty. It's that the tone is kind of intimate. I would have to say it doesn't sound like the first text they'd exchanged since 3 weeks ago and I think you may be suspecting they've been chatting regularly during that time. I would.

But the only answer is what the others said. Have it out with him and clear the air.
posted by zadcat at 9:15 AM on October 14, 2012 [16 favorites]

I agree with those who call this borderline flirty. The reason is, I could see sending those texts if I was flirting with someone. On the other hand, I could see sending those texts if I was not flirting with someone. A lot depends on context and the conversational style of the people involved.

If you have no other indications that your boyfriend is inclined to cheat on you, then I would say that you are way over-reacting and jumping to the worst possible conclusion in the absence of evidence. You say that you suffer from depression - one effect of that condition is the tendency to assume the worst. You may want to account for that bias in evaluating your fears.

This is not to say that he definitely isn't flirting with D, of course. I'm just saying that your available evidence right now is a minor warning flag at most.

I also agree with Georgina's advice to drop the idea that you have "squandered your youth." Whether or not your current relationship ends up lasting for decades or blowing up next week, you haven't wasted anything. For one thing, you are still quite young. For another, if your years with SO have been happy and rewarding then they were not wasted, whether or not the relationship lasts the rest of your life.
posted by tdismukes at 9:21 AM on October 14, 2012 [1 favorite]

I was just curious to get some outside opinions as to whether the texts were flirtatious

If it's soooooo cold outside, how did he leave his jacket at her house anyway without realizing it the minute he stepped out the door? Maybe I think that is such a blatant move because that is MY go-to move when I want an excuse to see someone in person again. But I don't know, to me it's kind of a cliche to start with.

But then, the texts. Texting a girl late at night about how drunk you are and how you really really wish you had that thing that you left at her house? Come on. Seriously. That is like classic behavior of someone who wants to hook up, to me.

Quite honestly, I have NEVER received a text, phone call, IM, etc., from a guy, talking about how drunk he is, without the topic quickly changing into how horny he is. But the whole combo of, "I'm drunk," "I really want that thing I left at your house right now." and bringing up talk of nakedness... to me, that is quite firmly in the territory of trying to make things go in a flirtier or sexual direction.

The only good thing about this is, judging from her replies, D has ZERO interest in him and is trying to shut him down. It doesn't sound like she's interested in any way, odds are she sees him as a really creepy old dude who she wishes would stop texting her.

About what to do now, I think if you bring it up now, rather than waiting to see if he does something more overt, you will most likely get one of the two classic responses: "How COULD you read my texts and you just don't trust me and you are the untrustworthy one." Or, "What?? I just sent her a text reminding her I need my jacket and you are jealous over that?? Really??"

I still think it's good to bring it up now, because he could in fact make a really good reply that sets your mind at ease. But if he gives you a defensive reply that is all about making you the wrong and bad one, then you just watch and see what happens. If he keeps doing things that set you on edge, you don't need his agreement that they are problematic in order to decide for yourself that they are problematic and you might want to re-think things with him.
posted by cairdeas at 9:23 AM on October 14, 2012 [33 favorites]

If it's soooooo cold outside, how did he leave his jacket at her house anyway without realizing it the minute he stepped out the door?

The weather in New York has been really weird for the past few weeks, so it's entirely possible that he wore a jacket somewhere 3 weeks ago, found that it was warm enough that he took it off and entirely forgot about it, and now it's suddenly 45 degrees out in October and he wants that jacket back.

That said, there is a lot of truth to what caideras says. Also, leaving an object at someone's place and then making a big show of getting it back is classic "I like you and I'm looking for excuses to hang out" behavior.
posted by Sara C. at 9:45 AM on October 14, 2012

i am an extremely conservative person. that being said, there's a big difference between flirting and cheating on someone. If you feel flirting is cheating, that's something that needs to be discussed because not everyone feels that way. If you think flirting is wrong, that also needs to be discussed.

If the real problem (which it would be for me) is whether flirting means he would cheat on you, then that's step 2. "Ok, so you think flirting is ok. Well what is the line that if crossed, means that one is cheating?" is a question to ask. Agree with nile_red that the reactions you get to these questions will likely give you the answers you're looking for if you pay attention.
posted by saraindc at 9:53 AM on October 14, 2012

I think if you're crying from this experience, a part of you picking up on the fact that he does have lower limits in terms of how much younger a woman he would go for than you previously realized. I say this because perhaps you felt a certain sense of security in this relationship thinking that you were the lowest limit of what he would seek in an attainable partner, thus securing you as cherished indefinitely (this based on the notion that men are happiest in having a youthful partner, which I feel society does condition us to believe)

FWIW my sister (mid 20s) also dates older men in the 15+ years range. The last time it went downhill I tried gently pointing out that age is just a number -- just because he's older physically doesn't mean he's older mentally/emotionally (which is often her rationale for dating older, cuz they're "more mature" than men her age). He could be 50 on the outside, but still operating at a 15-year-old mindset on the inside because that's where he got stuck in life. So while my sister matures in her earnest effort to be the best she can be in a relationship, her effort is not often reciprocated because of the mistaken belief system she shares with her partners: that because they're older, they don't have as much self-work to do --when I believe in reality it's the opposite (because they're older, it's actually evidence they have a LOT of self-work to do, but rarely do my sister's boyfriends agree that this is the case). I also think that with such a guy, he'll probably continue to gravitate to younger women who match his mental-emotional level of maturity, because that's the perspective from where he can relate. In other words, he's not maturing alongside his partner; he's staying where he's at while his partner tends to mature beyond him. Just my opinion though.

Anyhow, I hope that gives you some food for thought. As others said, if this is the beginning of the end, it's NOT time wasted. It certainly hasn't been for my sister. Best of luck, OP!
posted by human ecologist at 10:20 AM on October 14, 2012 [17 favorites]

Those texts don't appear very flirty to me, so I think you are overreacting. Talk with him about his contact with D since it bothers you, but don't frame it as a fidelity issue to start with.
posted by springload at 10:29 AM on October 14, 2012 [1 favorite]

I agree that the texts are, at the very least, occasion for you to raise the question as to what the nature of their friendship/relationship is, and why he wasn't comfortable being open with you about it. None of us can know what's in his mind, but they are occasion for this direct conversation. And you need to have it. Bottling up your fears is poisoning you and giving you too much mental space to completely catastrophize. You need to find out what you're dealing with. Just fess up that you saw the texts, they seemed intimate, and it's raised your concerns.

I've squandered my youth on this older guy and now he's moving on to a girl younger than me and making a fool out of me.

Definitely stop thinking this way. You're under 30. You still have your youth. Also, do you want to squander more of your younger years by not knowing the truth? You owe it to yourself to explore, not overlook, this question.

He could be 50 on the outside, but still operating at a 15-year-old mindset on the inside because that's where he got stuck in life.

This is such an important point. I know there are some relationships with a large age span which are healthy and work, so I never say never, but I'd say they are more of the "20" in the 80/20 rule, whereas the 80% are relationship where the older man selects younger partners for reasons of incomplete personal growth. So I'd ask you this. Where is your relationship going? After 4 years (that's a long time) you don't cohabitate. Are you happy with the reasons for that? Do you plan/want to get married some day, or at least have a formal life-partnership? Is that his plan too? Have you talked about it?

If there's no long-term vision for this relationship, then that might be serving him very well. He may want to never settle down, in which case it isn't out of the question for him to be musing about potential other, younger partners who won't be pressuring him for a future, and will still idealize him for his perceived maturity.

So I'd just say that even the fact that this question occurs to you, and you don't seem to feel at all secure about your own future together or his commitment to you as a person, rather than his contentment with you as "younger girlfriend," is a red flag that it might be high time to have the "what is this about and where do you see it all heading" conversation.
posted by Miko at 10:49 AM on October 14, 2012 [5 favorites]

I agree with everyone who's said that the texts do seem a bit flirtatious, but disagree that an open conversation on the subject would be particularly useful at this point, given the subtlety of the tone. If he was flirting, he'll likely be guilty and defensive; even if he wasn't, he'll likely be embarrassed and reluctant to talk about it. Either way, there's a high probability of getting an angry evasive counter-accusatory exchange that gives you no actual information about SO's mindset.

If you were to mention tomorrow that you're headed to the post office, and casually ask for D's address so you can send her postage to ship his jacket back, do you think he'd happily comply and be glad to have the whole thing over with? Or would he make excuses so he can set up a return scenario where he gets to meet D again?
posted by Bardolph at 11:03 AM on October 14, 2012 [1 favorite]

I'm going against the grain here and say that I didn't see anything flirty in those texts at all. If I saw my SO texting someone with those exact texts my reaction wouldn't have been to cry or feel betrayed, I would have joined in the conversation and talked about when we should get his jacket back or sumthin'.

So, yeah, my opinion is that you're way overreacting. Calm down and find out and talk to him before you toss away your relationship based on this texting business. Guys can have female friends, especially if they've known each other forever (she is his best friend's daughter) without it being a betrayal or cheating.
posted by patheral at 11:11 AM on October 14, 2012 [2 favorites]

Definitely flirty on his side. I'm actually surprised some people are saying not flirty. Cairdeas hits it on the nail -- late night, mentioning drunk, mentioning naked, hope you can sleep (hoping that D will respond that she is in bed, about to go to bed?). I wonder if there is a gender skew in the reactions to the question of whether the texts are flirty. I was long ago a thin, attractive, 21-year-old female, and like most in that category I got a lot of attention from older men for several years. I remember what it sounded like. Definitely flirty. (Though not too creepy, which is good news.)

Not flirty at all on her side (which is good news for the situation).
posted by ClaudiaCenter at 11:44 AM on October 14, 2012 [4 favorites]

Dansaman's approach is really a good one, too, I think, if you want to make this less a referendum on your relationship and more like a smack on the back of the head.

Let's pull this back from "is it flirty?" and squarely into "it's inappropriate" and, further, as his significant other, you're uncomfortable. If I found out my best friend was texting my kid, I'd rip their throat out. It's bad territory to be in and your SO is not showing good judgement. Go with him to get the damn jacket and suggest that he delete her number from his book.
posted by amanda at 11:53 AM on October 14, 2012 [3 favorites]

They don't sound flirty to me, but you don't have the full story. To me it sounds like he's having a faux-melodramatic dig at her because she still has his jacket. You don't know who texted who first but if you were asleep/trying to sleep on the train he might have been bored and a 21 yr old girl is probably more likely to respond than someone you might have found more appropriate for him to be texting. You don't know how many people he texted first, or if she texted him first. Its been 3 weeks since he left his jacket so if it was a move, sounds like she's shut him down and hasn't let him come back to get it (hence the digs) - even if it wasn't a move that could be the case, she could be genuinely busy or she might just not be comfortable with him visiting her in her apartment, alone - we have no way of knowing what the situation is. Of course if she did want to get him out of her life she could have presumably given the jacket to her dad to give to your SO. Maybe she enjoys the attention or maybe she just enjoys talking to him, I remember how guys her age can be! Maybe its the other way around, maybe she's flirty with him and he's enjoying the attention. Wouldn't you? Even if you had no intention of cheating?

There are just too many variables to call it without knowing all the facts but I suspect that you may be oversensitive because of the age gap. My So is 11 years older than me (and yeah, my friends said I could do better etc), I suspect you're concerned that he's looking to trade you in for a younger model.
posted by missmagenta at 12:18 PM on October 14, 2012 [2 favorites]

Nth-ing that for me this would not be a huge huge deal and that I would express my concern without blowing it out of proportion. They are a little flirty, yes. It's inappropriate that he is texting and flirting with a 21-year-old, yes.

How would you feel if he was sending these texts to a female coworker? A mutual female friend? His female best friend from college who you've never really liked? The context is really important, and this is a context that would make me a little concerned.

I don't think flirting is cheating, and I think it's ok for both me and my SO to flirt a little occasionally with other people. But that's me, and it's totally cool if you have your own definition of what's cheating and what's inappropriate - as long as you communicate about it and make it clear to him.

I would just straight up call him out. When he asks why you're acting weird or if everything's ok, just be real: "Last night on the train I saw you sending those flirty text messages with D. I know it's just texts and I trust you, but I think it's kind of creepy and weird - I don't want you to be that creepy dude who flirts with his friend's daughter. She's just a kid. D and BF could totally interpret that the wrong way. And it made me feel upset and really weirded out." Pause. "I don't send flirty text messages to other guys, because I'm committed to you. I don't want either of us to be sending flirty texts with other people."
posted by amaire at 12:27 PM on October 14, 2012 [3 favorites]

Yes, they were flirty, yes, you should bring it up to him ASAP, and yes, you are overreacting.
posted by treehorn+bunny at 12:43 PM on October 14, 2012 [3 favorites]

It is flirty. Whether or not she has any interest in him (doesn't sound that way), he seems to have some for her, or at least is thinking about her. The fact that he said he was "out late watching the game & I'm a little drunk" & did not mention the fact that he with you, is alarming. Someone who acts like they're a couple would say "we just finished watching the game, had some drinks". Someone who's not feeling that way wouldn't want to mention that they're with they're girlfriend. It seems like an easy miss, but you wouldn't want to mention to someone you're interested in that your out with your girlfriend, you'd want her to think you're alone. That & the gratuitous naked comment (definitely testing the waters), & the other comments add up. Either way I think he's enjoying/entertaining the fact that he has this communication from a younger girl (as you stated he is a lot older than you so this does seem to bring up a pattern). The good side is that from what you mentioned the girl doesn't seem to be returning the flirtation with him. Patterns are important. I had an SO who was older than me & I also in a weird way thought I was probably the limit for the lower age, & that I was magically somehow the right one. Later after my SO turned out the be quite the dishonest one & slept with someone 15 years younger, I found my thoughts of being the one quite ridiculous. I had the feeling to be upset at little clues like you have, & I felt so strongly that something was wrong, because something was. I'm not saying that's the case for you or that he's cheating, but I think you're aware that deep down your mind is telling you that something's off. It also could be a mix of your insecurities coming into play, that he would find someone else & leave you for someone younger. Now you feel it's happening, or quite possible. Either way you need to talk to him. Look at his past history, is he an honorable guy or does he have a shady romantic past? These are good indicators of future behavior, although some people do learn from their mistakes. Also look at his family, a lot of times the apple doesn't fall far from the tree, as we do learn a lot about what love is & what's acceptable on how to treat your SO. Definitely talk to him. You can't really know what's going on or gauge his reaction to what's going on unless you do. Only you can figure it out, but you must talk to him about it. Otherwise if there are some feelings then not addressing it will probably help it along. Don't ignore anything you have issue with. Talk to him about it. I truly hope it all works out, & there's no cause to be alarmed. Finding someone you love is great, but don't let love cause you to be blind. Trust if there's reason to, but also trust your feelings, & examine exactly why the reasons are that you're having such a strong reaction to this.
posted by readygo at 1:18 PM on October 14, 2012

I'm not an expert at answering any of your questions except one: Yes, those texts were flirtatious. Definitely. (Whether they were 'flirtatious with intent' or not is really a question that can only be deduced with more information or by asking him. But they're definitely flirtatious.) Talk to him and find out if there's intent.
posted by Kololo at 2:47 PM on October 14, 2012

What do you know about his past? Or how much do you know about his past? That is a good indicator of his attraction to younger women. Frankly it is flirtatious and he is into women much younger than him which might be his attraction to you. Take stock if this is what you want. Sooner your later you will grow older and this man may not find you the "ideal" partner for him. My guess is he will dump you much before that. He does has the right to chose younger partners, you might just be fighting against some basic attraction here. Also whether we admit it or not, in some cases, we have already seen red flags and things like this bring those up all in a single go. This might be stirring some of your already existing suspicions
posted by pakora1 at 3:10 PM on October 14, 2012

I'm just going to throw out some random thoughts here, I hope they're helpful:

Are you being treated for the depression? If depression is part of the bigger picture, then it might be tough for you to judge this incident in perspective. I hope you're getting treatment and that, in conjunction with treatment, you are being as good as you can to yourself right now -- whatever that means. Self-care like getting enough sleep, baths, talking to a good friend, going for a walk outside in the sunshine, listening to relaxing music, etc. Whatever you can do. I know this may be too much for you.

Your reaction seems to blame yourself -- quasi-snooping? Really? You looked over and saw what he was doing. I kind of think it's a convenient mind-trick for you to excuse not saying something at that very moment. Maybe that's a pattern in your relationship with him. Maybe that's a pattern you have regardless of your relationship with him. You might want to look at that.

I don't know you, so forgive me if I'm assuming too much, but if you feel upset, keep it to yourself and then ruminate to the point where you are feeling "out of control and helpless and angry and hurt," it's not serving you. At the other end of the spectrum are people who would flip out and start a fight right then and there. There's something in the middle and you can find that middle ground -- noticing how you feel in the moment and expressing it. It can be difficult to gauge how upset you "deserve" to feel. It's not a question of deserving. If this upset you, it doesn't matter what anyone else thinks. Your feelings are valid.
posted by Majorita at 3:29 PM on October 14, 2012 [1 favorite]

Flirting. For full disclosure, I dated a ~40-year-old man from ages 18 to 20. So I'm both sympathetic to your perspective and a bit wary of May-December romances, since I know how they can can go sour.

I think if I read this over my boyfriend's shoulder I'd feel hurt too because
1) Going from "no jacket/scarf" to "naked" is a leap someone in a horny frame of mind would make,
2) He's out with you but he didn't mention you (or "we" or "us"), again, something someone nursing a horny night-texting crush would do, and
3) He seems to have been texting her for awhile, and hasn't said anything about it to you for 3 weeks.

So honestly, I would be a bit annoyed and would bring it up with him ASAP. It seems like you're very devoted to him and it shocked you a bit that he'd have any interest at all in sneaking around like this to flirt a bit, and I think those feelings are justified-- you're allowed to want a partner who doesn't go out of his way to send sexy texts to a young girl he just met. Even if it's not technically "wrong" yet, it's not something I'd want to be on edge about in the long-term. You're young, you can find someone else who doesn't do this.

At this point though, what you really need to do is talk about it with him.

To editorialize a bit more: after leaving my first and only "age gap" relationship, I would never start one again. I would be a little bit harder on an older boyfriend because conditions really have to be perfect to make all the difficulties/sacrifices worth it, to be honest. Also, because it's often true what others have said here about older men who date younger being "frozen" at a certain age of maturity and eventually falling behind their younger girlfriends. The worst thing about it is that you can't tell for a long time. And once you're in, you've created so many mental bulwarks against the "mainstream" objections to age gap relationships that it's hard to go back on those or see it from your original perspective. Like a more advanced version of the sunk cost fallacy-- you don't want to have wasted 4 years and you don't want everyone to say "I told you so" and you're convinced that the power dynamics, &c. are all under your control, so it's hard to judge rightly what to do, sometimes.
posted by stoneandstar at 4:49 PM on October 14, 2012 [7 favorites]

If it's soooooo cold outside, how did he leave his jacket at her house anyway without realizing it the minute he stepped out the door?

He left the jacket behind three weeks prior to the texting. We don't know if it was cold the night he left the jacket behind.

Me, I don't see anything "flirty" in these texts at all. I see "jokey" (he's jokily exaggerating his suffering as a result of not having his coat [he's "naked" without it]and her "guilt" at keeping hold of it all this time [how can she sleep at night?]). Obviously jokey texting could be symptomatic of a flirtatious relationship, but it could just as well be symptomatic of an innocently friendly one.

If he left the coat as a "ploy" to get some one-on-one time with her, three weeks seems like an awfully long time to wait to spring his dastardly trap.
posted by yoink at 4:50 PM on October 14, 2012 [4 favorites]

On one hand, I see a guy trying to sound young, hip and cool to a girl he probably thinks of as his niece or god daughter. On the other I see someone who might want to think about the magnitude of their reactions to their own speculation and may want to consider whether this is the result of lack of confidence in their position in the relationship of the relationship's long term outlook.
posted by rr at 6:26 PM on October 14, 2012

I read it as flirtation, though possibly both texters are thinking of it as very innocent. No one brings up nakedness in such a manner to someone of the opposite sex, and someone far younger, without there being at least a soupcon of a tingle. (Otherwise, "Ewww, my dad's friend is *such* a creep!")
posted by heigh-hothederryo at 7:14 PM on October 14, 2012 [1 favorite]

Actually, what zadcat said. There is at least an intimacy to be read here, and without a justifiable backstory. My antennae would be up.
posted by heigh-hothederryo at 7:17 PM on October 14, 2012 [2 favorites]

I've squandered my youth on this older guy and now he's moving on to a girl younger than me and making a fool out of me.

It's pretty common for your first long-term relationship to expire in your mid twenties, since you don't really know what to look for and who you are when you started. The biggest indicator for divorce is an early marriage, so I wouldn't worry too much about this. It's painful while it's happening but years later you will thank yourself that it happened (it it does end up in a split).

Don't think about being "made a fool" of. If the guy is a creep, DTMFA regardless for what anyone else says. It doesn't matter if you defended him yesterday if you find evidence of an affair today. Anybody who would mock you for that is not a real friend.

And yes, I'm voting in the flirty camp. My fellow paranoids above have detailed exactly why this is classic "I have a good excuse for staying in touch with you" behavior. The reason he hasn't picked up the damn coat in three weeks is it allows him to prolong the texting and flirting, and until he gets familiar enough to "drop by, get my coat, and btw why don't we grab a drink?"
posted by benzenedream at 8:11 PM on October 14, 2012 [1 favorite]

You sure best friend was with your SO at best friend's daughter's apartment that night?
posted by zippy at 11:33 PM on October 14, 2012 [1 favorite]

The jump to "naked", and the careful editorialising to remove all mention of your presence? Yeah, this is definitely flirting - and I'm genuinely surprised at the number of people who disagree here.
Whether or not this is significant depends on your relationship and likely a few factors unknown to you, but this is most definitely flirtatious.
posted by ominous_paws at 12:19 AM on October 15, 2012 [1 favorite]

Even if you confront your bf - what is he going to say that will make you feel better??

The level of intimacy in their texts is not explainable. Sorry.

The issue is that there is no great answer. You've just discovered your BF is not the guy you committed too, no matter what story he tells you about the text messaging.

How do you want to handle this?

Personally, I'd suggest a gentle exit. This is not the relationship you signed up for. You just found this out. Move gently and slowly out of this relationship. It's not what you thought it was.

This kinda stuff happens. It's OK to opt out.
posted by jbenben at 12:21 AM on October 15, 2012 [2 favorites]

I totally agree with jbenben except that upon re-reading, the girl really doesn't seem that interested. In fact she seems like she's being rather terse and polite. I would be disappointed in your boyfriend, though.
posted by stoneandstar at 1:17 AM on October 15, 2012

For polling purposes I will say I don't think you're overreacting.

Also, the forgotten jacket/hat/whatever is the oldest trick in the lame flirting book.

In the end, you and your SO have hopefully defined what is appropriate behavior or not through your time together. In my marriage, for example, we are both polite but distant to people of the other sex. If after years of this standard my SO started texting at night about being naked and leaving jackets at people's homes, it would be pretty obvious to me he's at least attracted to the woman in question (which wouldn't be a problem in itself) and not making an effort to control it (which would be the serious problem).

So, what I would recommend is trying to see this set of behaviors in the context of your couple's customs. If he is not interacting with this woman the way he has done for the length of your relationship, then suspicion is logical, I think.

And finally, to be honest, I wouldn't mention I read the texts. I would say I am not happy with the way he is interacting with D. Then I would let him think I know more than what I'm saying. Sometimes the appearance of being informed is as powerful as actually knowing, and if he behaves guilty or defensive, you have your answer.
posted by Tarumba at 7:29 AM on October 15, 2012

Also...you have the right to not like his behavior and end the relationship, even if he has a reasonable explanation for the texts (which I doubt , but if he does, I would love to hear it).

On the other hand, though, people fuck up sometimes. If he admitted he did and showed honest regret and understanding of how serious the mistake is, then continuing the relationship wouldn't be a must (it never is), but it wouldn't be a loopy idea, either. Sometimes these problems end up giving people the wake up call they needed.
posted by Tarumba at 7:41 AM on October 15, 2012

As a guy, I don't see anything flirty in that. I cross boundaries all the time with female acquaintances or friends, and my male friends cross boundaries all the time with my girlfriends. I have strange friends.

My girlfriend occasionally gets slightly bent out of shape about the line crossing. As an example, two things happened at the bar when I was there by myself with friends a few weeks ago. First, it was Oktoberfest celebration at that bar, and I know two of the female bartenders well. They were all dressed up for it in bows and dresses and pigtails and whatnot. I tugged pigtails and snuck up behind them and untied apron strings and innocent things like that. My girlfriend wasn't OK with me "flirting" with the bartenders ... I wasn't, I was making their lives difficult, and it's OK because we're friends outside of the bar and they know that I can't resist the temptation to make other people's lives difficult. The second thing is that one of the couples I hang out with lives across the street from the bar's patio. The couple exited their front door, with the female member of the couple still adjusting her bra, and the entire patio exploded into spontaneous applause and cheering as apparently the couple had been enjoying sexyfuntime. A few people jumped up as the female member of the couple came onto the deck and escorted her to her chair as if she was royalty, I held her chair for her and bowed as she took a seat. She was bright red in the face through the entire thing and the entire patio was laughing.

She (my girlfriend) sees all of the above as flirting. It's not. I enjoy teasing people. I find it funny, and once in a while other people do too. I do things that I find funny because I enjoy laughing and making other people laugh. I try to pick my moments and tease people I have conversed for at least a few hours with so as to not make people feel awkward or uncomfortable; but sometimes I also use teasing as a way to get over an uncomfortable situation or to help someone else get over an uncomfortable situation. The female member of the couple at the bar was extremely uncomfortable that everyone knew they had just been shagging; some people knew knew them were uncomfortable with the idea that they came to the bar freshly postcoital; by treating her like royalty we helped everyone laugh and get over their uncomfortableness.

To me, what your boyfriend was doing looks like he enjoyed talking to her the other night, and it was uncomfortable for him or possibly for her that he had to go back and get his jacket later. He used humor to defuse it. Not all uses of humor by a man towards a woman are flirting.
posted by SpecialK at 8:55 AM on October 15, 2012

Mod note: This is a followup from the asker.

I'm pretty ashamed of this, but I totally grabbed his phone yesterday to see what kind of correspondence he's been having with D. Apparently this is how it's gone:

SO (on Thursday last): Hey coat thief, are you around tomorrow or Monday?
D: Nope, heading back to ATL tonight, I'm on fall break!
SO: Ok, don't feel bad for me freezing to death.
D: Sorry dude! When I come back we can meet up and I can return it.

which was then followed by the text exchange from Friday night:

SO to D: Damn cold outside, wish I had my jacket.
D to SO: oh dear, I hope you at least have a scarf.
SO to D: Naked through the streets of NYC. Hope u can sleep 2night.
D to SO: drama queen
SO to D: maybe a little bit. stayed out late watching the yankee game. a little drunk.

I don't trust myself anymore - I think my depression/anxiety are raging out of control, and those who have pointed out that this might be indicative of my not feeling 100% secure in this relationship are on to something - I've been with him for four years and it doesn't seem to be progressing towards anything officially longer term, which wasn't a dealbreaker for me when we first got together but is becoming so now. But at any rate.

I'd think, based on the whole text conversation, that she's pretty not interested - which doesn't surprise me, because ew, dad's best friend. Am I reading this correctly? Like I said, I don't trust myself anymore.

And I'm really disappointed in him. I don't know what I'm going to do from here, but I appreciate everyone's perspective.

posted by cortex (staff) at 9:24 AM on October 15, 2012

I'd think, based on the whole text conversation, that she's pretty not interested - which doesn't surprise me, because ew, dad's best friend. Am I reading this correctly?

I agree with your interpretation of her responses. I actually don't find the first series of texts flirtatious at all, I could see an uncle/dad's best friend figure sending me those texts without weirding me out--they are jokey, not flirty.
posted by sallybrown at 9:32 AM on October 15, 2012

Oh yeah, she's definitely not interested. "Meet up" so she can return the jacket means "not interested in you coming to my place and prolonging this."

Your instincts are on target. But you need to not snoop. You need to not let your anxiety make you snoop. You need to trust the vibes you read, trust yourself. And extract yourself from situations/relationships that feed your anxiety, starting with this one. Because you deserve better, first of all, you deserve a guy who says "hey I left my jacket over at BF's daughter's place, let's go pick it up and we'll all get a drink together, you two would get along great!" And because in this relationship, trust is now gone. You don't feel safe about his surreptitious texting and you are surreptitiously reading his texts. Not good on either side. So move on and deal with your anxiety on your own before getting into another relationship. You deserve to take good care of yourself.
posted by headnsouth at 9:34 AM on October 15, 2012 [3 favorites]

You're probably accurate about D's (lack of) interest. It's still not clear what your boyfriend was doing. If he doesn't text a lot, maybe this was just his idea of how people do it. Above all, though, it sounds to me like this is an ideal opportunity to consider whether this relationship is what YOU want for the future. Take back your agency!
posted by BibiRose at 9:39 AM on October 15, 2012 [1 favorite]

Whether or not D is interested is not the most important thing (she doesn't sound interested). Is SO interested in wandering and has that manifested itself in his coorespondance with D? I would just tell SO that you were upset the other night becuase you noticed he was texting D. Be on alert for gaslighting.
posted by WeekendJen at 10:44 AM on October 15, 2012

I'd think, based on the whole text conversation, that she's pretty not interested

She's not. But I think he is. The playful tone ("coat thief") pity-me attempt ("freezing to death") and the fact that he didn't just set up a time and place convenient for her to retrieve the coat, in a straightforward way, indicates to me that he's at least fishing in these interactions. She's obviously not playing along in way that indicates things going anywhere.

But I'd still, just please, have the conversation. Have it now. DO trust yourself! There are good reasons why you're concerned. You're not comfortable, you're not happy, he's kept from you that he's trying to develop an ongoing friendship, and you're unsure about the future of your relationship. This is all you need to have or know in order to bring to your relationship the attention that it needs right now.

If your relationship is healthy and resilient, and you're both full participants and want to stay together and have this grow in intimacy, then there's really nothing to fear - you'll get through it together fine. This is a normal kind of interaction that happens in long-term relationships: "Something you did is making me feel uncomfortable/jealous/insecure." "Well, here's why I did it and how can I help you feel better/here's the issue/ here's what I need from you." Normal stuff. Don't let it scare you or ruin your composure.

If it doesn't go as well as all that, then it's a normal kind of interaction that begins to give a person concerns about whether the relationship is strong. You aren't going to be destroyed either way. You're a whole person, more than this relationship. If your fears of loss are paralyzing you, recognize that you are going to be all right, no matter what - but you shouldn't keep subsuming your real emotions and concerns to the idea of not rocking the boat, or questioning yourself.

It's fine to feel jealous from time to time. It's a normal part of being someone's partner. What's not fine is not acting on it out of self-love and self-respect, and trying to find a solution that returns you to emotional balance.
posted by Miko at 10:47 AM on October 15, 2012 [7 favorites]

Sneaky texting (when he thinks you're asleep) is a Big Red Flag.

How is this sneaky? She's asleep on the train, so he's not allowed to text? "Sneaky" would imply some sort of deliberate attempt at concealment, not texting when she happens to be

The playful tone ("coat thief") pity-me attempt ("freezing to death" )

"Playful tone" describes most people's interactions with friends of their parents.

The entire message history actually makes this seem more innocent, not less.
posted by spaltavian at 1:30 PM on October 15, 2012 [2 favorites]

"Playful tone" describes most people's interactions with friends of their parents.

it's his playful tone - interacting with a child of his friend's. Different. If anything she sounds much more in control of her communications.
posted by Miko at 1:49 PM on October 15, 2012 [1 favorite]

I suspect sneaky because it sounds a little too casual, because it mentions the evening's activities without mentioning being with OP, brings up nakedness out of nowhere, and a casual "hey I'm bored on the train lets text" level of friendship was previously unknown to OP. I'm not saying that relationships have 100% disclosure of all conversations, but three weeks is a while.

I'd definitely agree that HE seems flirty, and the daughter seems to be shutting it down. I've been in a situation where an older guy contacted me in a flirty way without me bringing the conversation to that casual level - it can be awkward for the younger girl.

From my perspective, the bottom line is this: Is this similar to how your relationship started? Do you think his flirting tone in this or any other conversation with a younger girl is something he'd act on, or become a situation he entered with the intention of friendship but develops into something else?

I ask because this was my main avenue to cheating. Texting when I had opportunities to not be questioned about it, playful casual flirty sorts of tone, then hanging out, and then eventually, bam! Oops! Didn't know it was gonna happen, didn't intend, so sorry etc. For a while, I wasn't able to be honest enough with myself to realize it was a pattern, and I convinced myself it was several one-offs, something that I just kept accidentally falling into.
posted by nile_red at 5:16 PM on October 15, 2012 [1 favorite]

brings up nakedness out of nowhere

Oh FFS. It's not "out of nowhere." It is in response to "I hope you at least have a scarf." It's a jokey exaggeration of the consequences of her having held onto the coat for so long. There are very few men in this world who think the mere concept of them being "naked" will be an automatic turn-on to a random girl.

This is 2012, people. Men can mention nakedness to women without necessarily being unspeakable bounders who should be horsewhipped for their moral laxity.
posted by yoink at 6:03 PM on October 15, 2012 [2 favorites]

Sure, it's jokey, but it seems to be flirty-jokey to me, which is just an opinion.
posted by nile_red at 4:14 AM on October 16, 2012 [1 favorite]

The jump from no scarf to nakedness was a big jump, and a bizarre one at that (when I read the texts, it took me a minute to even realize how "nakedness" fit into the conversation at all). I also don't think a man with innocent intentions would mention nakedness in a conversation with his friend's college-aged daughter. Even if that isn't evidence enough that these are majorly flirty texts, you also have the reference to being drunk, the lack of reference to the fact that he was out with his girlfriend rather than out alone, and the fact that this conversation happened late at night. I'm surprised that people think this exchange wasn't flirtatious, because it seems like classic flirty texts to me.

Oh, and +1 to the notion that leaving a jacket at her place is a classic excuse to see her again. Of course it's possible he left it innocently as well, but when you combine it with the flirting over text, it looks less likely that it was innocent.
posted by whitelily at 6:33 AM on October 16, 2012 [2 favorites]

Have you been cheated on before? Do you have the sense that he is likely to cheat? Because your reaction makes some sense if either of those things are true. But if not, I tend to think you are overreacting. If the fellow described were a particular ex of mine, yes, that would be A Sign and I would know that, and be upset. Because of a years-long pattern of behaviour on his part. However, if it were my husband, I wouldn't give it a second thought. (Even before we were married.) I could also see myself texting such a thing to someone in a completely innocently flirty way. Yes, there is such a thing. Just because one is a little bit playful when talking to a member of the sex to which one is attracted does NOT mean that one is only awaiting the first opportunity to jump into bed with them.

On the other hand, if he's like my ex, it's definitely something to worry about.

Really, this comes down far too much to your boyfriend's usual personality and conduct, and the state of your relationship, for the internet to answer. We can't know a lot of things it's very important to know in order to evaluate at all. Basically, go with your gut. Your gut is telling you that this is A Problem. Either you are right, or you are wrong. But, from personal experience, if you're getting so suspicious and upset because of texts which are, on the surface, pretty innocent, the trust isn't coming back.

Unless this is a temporary thing brought on by the depression. Also a possibility. So many variables with which I have experience, and which I know can alter the situation in ways impossible to describe to anyone else! Yikes.

Can you ask your IRL friends? Have they gotten to like your boyfriend in the time that you've been dating? (If not, big red flag, again from personal experience.) Make sure they understand that you need them to be honest with you-- if they don't like him, they'll probably try to be diplomatic, figuring that you've already made up your mind to disregard their opinions and it's more trouble than it's worth to try to speak up. But they know the situation far better than any of us, and they may have really useful things to say. If they think you're overreacting, you probably are. If they say, "yeah, um, he's actually said some pretty inappropriate things to X while I was around..." obviously things are different.

Good luck.
posted by Because at 8:27 AM on October 16, 2012 [2 favorites]

I really agree with Because. Look how split the assessments of this are. In the past, when I've reacted to certain behavior with a feeling that it was very very bad news for the relationship, it's been either 1) because it fit a pattern that was now becoming clear, or 2) it was time for me to own that someone's behavior or attitudes did not sit well with me for whatever reason, and I needed to stop freaking out over what they were doing and start to explore how I was feeling.

There are so many possible explanations for this stuff, some game-changing and some not, but no matter what, the decision ultimately comes down to you.
posted by BibiRose at 8:39 AM on October 16, 2012

A single personal-opinion datapoint here:

1) She seems totally not interested, but trying to be nice. She was specific about "meeting up" for her to return the jacket, as opposed to "you can come over and get it."

2) I'd be very, very unhappy seeing this sort of correspondence from my husband. It would fire up a pretty big fucking hairy "We Need To Talk" conversation, and who knows what after that.

I'm not by nature a jealous person at all. I'm also not a dumb person. My husband has a ton of women friends and acquaintances (in addition to his male friends), and because of the nature of his work, quite a lot of them are gorgeous, charismatic, socially adept young women (actresses) with whom he works intimately, and often has playful and jokey (but not suggestive) repartee. Not a problem.

Not even a problem if he gets little crushes sometimes, because I'm not even sure how that could not happen among people, and I expect that it will/does happen. It matters a lot how he acts or doesn't act on that.

He's also very attractive (past middle age now, but was also of the "gorgeous" variety, and still damn good looking), charismatic, intelligent, talented, amusing, friendly, kind, etc. – and so people of all genders and ages are drawn to him generally, and he loves that. And I don't care; I feel happy about it, and not worried, because [Many Many Reasons]. But if I saw the same texts, I would be seriously not a happy camper.

People who recognize subtext recognize subtext. She does. She is avoiding his overtures and making it clear that she's not going to be inviting him over. You do, and you are upset and worried. I do, and I don't think you are in error.
posted by taz at 4:33 AM on October 17, 2012 [9 favorites]

At first, I read this with the characters switched around. I was thinking "she might be trying to flirt, but he's not biting."

Then I realized. D'oh.

Then I see he's done this on two occasions, and as cairdeas points out, embedded in this is an opportunity for him to go and see her, and it does kind of look like flirting in a "hey, could I come over and get the jacket I forgot" just doesn't.

Furthermore, he is doing something that looks like flirting and looks like fishing for a teehee! coyly! contrived! excuse to visit! with someone he should be actively avoiding talking to like that - his friend's daughter. Ew. If this were one of his own peers I'd be thinking "dude, watch it, this could be taken as flirting" and not necessarily be very suspicious of it. But with this girl, it's unambiguous, because she is such an inappropriate target.

Sorry, but I think you are seeing this for what it is. I don't think it's just your depression talking.

I also say this as a very unjealous person, and my default assumption is that flirting is not taking place unless proven otherwise. In this case, I do think it's proven otherwise. Sorry.
posted by tel3path at 9:30 AM on October 17, 2012 [1 favorite]

I could also see myself texting such a thing to someone in a completely innocently flirty way

If it were my boyfriend texting a female friend, I might raise my eyebrow, but wouldn't worry too much unless it became a weird pattern. But as a "young woman," if my dad's friend started texting me like this, I'd be pretty wtf. And I'm used to teasing from my parents' friends, just not teasing about nakedness, and late-night texts about how they're a little drunk. TMI.
posted by stoneandstar at 8:05 PM on October 20, 2012 [2 favorites]

Also, yeah, "meet up." I had an almost hook-up in college who borrowed me a book, and I didn't return it for three years, because everytime I proposed we "meet up" he made it sound like I'd be coming over to sleep with him first, and for Christ's sake, I just wanted to hand it off in a public place. I very specifically proposed "meeting up" each time.
posted by stoneandstar at 8:07 PM on October 20, 2012