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Whether and how to tell my shy, older friend I like-like him?
May 4, 2012 4:50 PM   Subscribe

Help me decide whether, and how, to man up with a shy friend I like-like with a significant age gap. Cue the snowflakes.

So I have this friend and he's an awesome person. Kind, generous, good listener, similar values, and I feel like a better person around him. He is also quite shy. I'm debating whether to tell him I like him as more than a friend, and I'm hoping you fine people will help me weigh the ins and outs. (I know there are existing questions related to mine but I feel mine has some mitigating factors so why not make a fresh start in asking.)

Before you comment, please know I am fully aware that I'm over-thinking and trying to predict the future. I just want to make a conscious, conscientious choice - so that means trying to think through all the different sides and potentials. I think my reasons for trying to think this through so much are very good, valid reasons. It isn't natural to me to think things through in this way, so it probably comes across like one of those girls who pictures marriage on a first date. If I don't look at these aspects - even if I look like a crazy fast-forwarder - I could make a poor decision. And that's where you come in, MeFites.

Sources of concern about confessing
* Maybe I'm misreading him.
He always responds to me and makes an effort to be around me in shared group activities. The last time I saw him he seemed to be fumbling on his words. Although I initiate much more, he initiates contact some - and it seems more than just friendly. On a particular website where we are connected, he has engaged me there more than any of my other friends over the last few months. Every time I invite our group to go do something he goes, or if he has a conflict, then he is clear about being eager to spend time together at a different time.

* I've been the pursuer before, in most of my relationships. (I'm a girl - and not too good at following gender roles, heh.) The last one where I was the pursuer made me feel resentful at being the one to initiate contact, sex, etc. about 95% of the time. Of course, in his case the lack of initiative seemed like laziness. In the case of this guy it seems more like shyness and innocence. But I already know there is a flavor of non-pursuer that irks me, and so I hesitate to risk the same patterns cropping up.

* He's about a decade older.
That doesn't bother me from a social perspective, and friends who'd judge aren't friends. He's a really awesome person, we've been friends for several months, and he could possibly be long-term material, but I want to be sure I think through the practical side of getting involved with a ten-year gap before I attempt to change our relationship.

For example, I might want kids and he's starting middle-age. I'll be able to have kids for about ten more years I think. Is it wise to pursue this from that standpoint? I'm not worried about the potential power imbalance in an age gap relationship because I don't think it applies here, nor am I worried about being treated like a child because I don't see that applying either. I'm not worried about the different cultural memories, because we were both pretty out of touch with all of that anyway. I am a little worried about differences in energy levels or the fact that he's known himself longer and is more established so I may look irresponsible by comparison in some respects.

* I don't want to mess up our social group.
Our shared group is tightly knit, and if we end up dating at some point they may find out, and if things go south I don't want the group to be weird for either of us. Also, things going south could make things difficult for either of us in another way, that I won't spell out for privacy, but let's just say it would be awkward city - and very publicly and obviously so.

*I don't want to hurt him.
My sense is that this guy doesn't have much relationship experience - at this point he is still too private about it for me to know for sure (another reason I think my sense is accurate). The last thing I want to do is try for something and then it looks like we aren't as compatible as I thought in the thick of Spring, and it ends. He's so cool... and if I'm reading the signals I think he is pretty into me too. So it would feel horrible in a worst-case scenario to know I was partly responsible for his heartache. And not just from the experience angle (though to me ending a relationship with a late bloomer is somehow worse than ending one with someone who's had many relationships) - I don't want to hurt him because he's an awesome person and doesn't deserve that.

Reasons I want to confess
* This is the first romantic interest I've had where I felt really stable about it and where I felt like being around the person made me my best self.
* There is something about his shyness that makes me feel really safe and that is a priority for me.
* I'm not sure how much more I can be around him feeling this way towards him without blurting it out or stealing a kiss or something. Plus, he's awesome and deserves to know someone is noticing.

TL; DR
Questions
1. Do you think I am reading the signals right?
2. I'm generally good at helping people feel comfortable, but is there anything else I can do to help my friend feel more at ease and less guarded about himself?
3. Asking shy guys (and others) for personal insight - If there is an existing friendship and fairly strong signals of romantic interest - would it put less pressure on a shy guy for a girl to ask him on "a date", or would it put less pressure on him for her to instead say something like she would not mind being kissed, leaving the labels and expectations of "dating" out of it? Also, would it be easier on a shy person to share this stuff in writing just before parting so they don't feel rushed to respond or would it be more appropriate to share when they could respond in the moment?
4. What are the practical considerations of a relationship between someone around 30 and someone around 40? How viable is it?
5. My interest in this person kind of caught me by surprise, and it is not so intense to make me feel crazy but I do think there is at least some portion of simple infatuation here. How can I make sure I make this decision based on the best interests of both parties, and not based on Spring fever?
posted by hungry hippo to Human Relations (35 answers total) 8 users marked this as a favorite
 
I understand where you're comming from. I am in a marrage where we have more than a decade age difference and it has been the best relationship I have ever had, infact, we are married and have been together for 8 years. You are obviously interested in this person, so why do you care about advice. Go with what your gut tells you, and you will be fine. There is way to much emphasis placed on age difference. It does NOT MATTER. You obviously feel a connection with one another, so, if you never persue this, you will never know and if your like me, I can't stand what if's. So don't waste any more time and have a great romance ! Do not become hung up on what others think because you will miss out on many things. Memail me if you have any other thoughts. :) trust me on this one.
posted by brittaincrowe at 5:09 PM on May 4, 2012 [1 favorite]


Age is irrelevant!
posted by mleigh at 5:16 PM on May 4, 2012 [2 favorites]


I am fairly shy -- to the point where I almost never ask anyone out unless I am fairly buzzed, or my friends basically tell me that someone is interested in me, and I have never, ever been intimidated by a girl who has asked me out, usually just surprised that they are interested more than anything else.

4. What are the practical considerations of a relationship between someone around 30 and someone around 40? How viable is it?

30-40 isn't as much of a problem as 20-30, and it gets to be less of a problem the older you get, I think.

Also, you sound like you have your shit together and know exactly what you're looking for, and that you should just go for it.

Asking shy guys (and others) for personal insight - If there is an existing friendship and fairly strong signals of romantic interest - would it put less pressure on a shy guy for a girl to ask him on "a date", or would it put less pressure on him for her to instead say something like she would not mind being kissed, leaving the labels and expectations of "dating" out of it? Also, would it be easier on a shy person to share this stuff in writing just before parting so they don't feel rushed to respond or would it be more appropriate to share when they could respond in the moment?

This guy sounds like he might just be a bit timid or maybe a bit dense, and just isn't sure that you are into him, so maybe being forward is just the way to go. Just invite him over to your place for dinner or something, and see how it goes. You don't need to be super forward, maybe just a bit of hand holding or whatever might break the ice enough for him to realize where things are with you guys.
posted by empath at 5:20 PM on May 4, 2012 [1 favorite]


(Honestly, just holding his hand while you're walking around might even do the trick -- that's how my longest term relationship that I've had actually started -- I had not a clue that she was interested in me as more than friends until she did that, and I never would have actually initiated that myself at the time)
posted by empath at 5:22 PM on May 4, 2012 [2 favorites]


Spring fever, yay! Eye contact! Hold it! Go for it!
posted by thinkpiece at 5:23 PM on May 4, 2012 [2 favorites]


Those who suggest hand-holding, I'm nervous to go at it that way. What if I'm misreading him? I would rather be rejected verbally than physically brushed off. I am one of those outgoing-shy people myself. It is easier for me to make a move with words than actions because I get so nervous about it. Maybe I can work up the nerve.
posted by hungry hippo at 5:34 PM on May 4, 2012


Why don't you just send him an email that says, "Hey, Selkirk, I had a great time with you at THING the other night. In fact, I always seem to have a good time when you're around! I would love to buy you dinner and get to know you in a more-than-friends kind of way, if you're up for that! How about DATE at PLACE? If not, I understand, and I hope we can still be friends when we run into each other at ACTIVITY!"

in re kids and stuff, you have plenty of time, and your kids might have to pay for their own college if he wants to retire when they're in high school, and that's assuming you wait another 7-10 years, but who knows what the world will be like THIRTY YEARS from now? don't borrow trouble before you go out on a single date with dude.
posted by Snarl Furillo at 5:41 PM on May 4, 2012 [7 favorites]


For all you know, he's thinking the exact same thing you are. In fact, I think it's most likely the case. And if that's true it would be a tragedy if no one made a move.

If you don't make a move, you'll always have regrets. If it doesn't work out, it sounds as if your friendship is strong enough to survive. Some times you have to take risks. Just do it.
posted by ShooBoo at 5:48 PM on May 4, 2012 [2 favorites]


No email! No big talks! No awkward one-on-ones!

It's time-honored, me-tested, successfully deployed: You are together, somewhere sunny. You are off, away from the group, talking, laughing. He says something personal, amusing. You look up from under your lashes, pause, and say, "Are you flirting with me?" OR you say something personal, amusing and when he doesn't laugh, you elbow him and say, "Hey, I'm flirting with you!" Then the eye contact. Boom.
posted by thinkpiece at 5:48 PM on May 4, 2012 [10 favorites]


There's something beautiful about this and your ask here.

1) Yes
2) You probably can't make him feel more at ease at first as a goal, but continue what you're doing plus.
3) It will be less pressure for you to ask him to, first, an easy semi-date, then a real date. (Example: ask/tell him you want to check out a new restaurant with him, no other plan than that.) No writing, that would really puzzle him at first - although he might figure it out and 'get it' - it will puzzle him and consume too much brain power until he does. If his birthday or some other rare occasion that could include a card comes up, you could write a short note in it, and nothing very long.
4) It can work, there are some small difficulties but nothing too bad. There are advantages too. ~30F and ~40M were my parents, and they stayed together all the way.
5) Date and do the normal things and see how it goes. By the way, Spring Fever is supposed to start things going like this.

As above, YES follow your gut!

Good luck!
posted by caclwmr4 at 6:01 PM on May 4, 2012 [2 favorites]


1) Most likely yes. So what if you're not?

2) He may become much less guarded once(if) you spend more time together. I have been that way, but that doesn't mean every shy person is.

3) In my opinion, ask him to do something with you alone, but not as a date, or leave that up in the air. Try thinking of something you know you both love to do. If it goes well, then try to push it forward. This happened to me once, I was 24 and she was 30, and it lead to a relationship that I will always cherish.

4) I don't see any problems here.

5) Enjoy the infatuation, have fun, give it some time.

In the case of this guy it seems more like shyness and innocence. But I already know there is a flavor of non-pursuer that irks me, and so I hesitate to risk the same patterns cropping up.

If it works out, maybe show him how you'd like to be responded to and see if he's teachable.
posted by Golden Eternity at 6:06 PM on May 4, 2012 [1 favorite]


You actually don't have to figure out about 75% of this right now. Questions about kids, social group, future, blah blah blah don't matter at all if he doesn't return your feelings. So don't get hung up on this stuff; those are bridges you can cross if and when you come to them.

You don't have to know the entire future and calculate every outcome to decide whether to speak about your feelings. With the benefit of hindsight in life, I say just go ahead and do it. It may meet your hopes, it may not, but you really have nothing here to lose. You can figure out the rest as it comes.
posted by Miko at 6:34 PM on May 4, 2012 [2 favorites]


Go for it!

Hand holding a problem? Lean up against him, side-to-side. Maybe just a bit ventral (versus dorsal), so that it'd be natural for him to put his arm around you. Are you shorter than he is? Slide up his body. It can be done super subtly, but crap, is it ever so sexy. Check his body language; tightening up? Nervous. Stepping back? Yeah, abort mission.

Don't worry if he doesn't. You say that he's shy, be a bit aggressive and possessive. Keep the body contact up and maybe place his hands on you for him.

That kind of behaviour isn't going to offend the vast majority of men; social inconveniences tend to only be significant if he is 1) really not into you, 2) you end up being really not into him. And 1) isn't a problem once you get over him and 2) Only if he turns out to be totally clingy, which doesn't fit the profile.

The potential positives outweigh the potential negatives.
posted by porpoise at 7:24 PM on May 4, 2012 [1 favorite]


So it would feel horrible in a worst-case scenario to know I was partly responsible for his heartache.

FWIW: About the only thing I've ever learned in life is that nothing worth having comes without some sort of risk and sacrifice. Nothing.

I can't tell you what specifically to do, but know this going in.
posted by 5Q7 at 7:25 PM on May 4, 2012 [2 favorites]


Golden Eagle - "3) In my opinion, ask him to do something with you alone, but not as a date, or leave that up in the air."

I've sort of done this. Most of the time I ask a group if they want to do X and on several occasions he's the only one to say yes. So the end result is doing X alone and then hanging post-X for a good chunk of time. My gut tells me I've kind of done this step - hence my back-and-forth about escalating....
posted by hungry hippo at 7:25 PM on May 4, 2012


Eternity, not Eagle, apologies Golden Eternity.
posted by hungry hippo at 7:26 PM on May 4, 2012


When you ask the group, he always says yes, no matter about others in the group, because he wants to spend time with you. Asking the group doesn't quite count for moving it up a step, because you had opened it to the group.

Ask him/tell him alone.
posted by caclwmr4 at 7:52 PM on May 4, 2012 [2 favorites]


I recommend you send very, very obvious indicators of interest--hair flipping, blushing, licking your lips, hardcore flirting, lots of smiling, open body language, bedroom eyes--until HE makes a move on you. I firmly believe that a lot of the anxiety in relationships is eliminated when the guy is the pursuer. Good luck!
posted by lotusmish at 8:16 PM on May 4, 2012 [4 favorites]


I wouldn't pursue this until you resolve the resentment you feel at always being the initiator, because there's a very real possibility that's what you'd be signing up for.
posted by headnsouth at 8:28 PM on May 4, 2012 [2 favorites]


I firmly believe that a lot of the anxiety in relationships is eliminated when the guy is the pursuer. Good luck!

Umm... I guess it depends whose perspective you are looking at it from. I'm a guy, and I have found that my level of anxiety in the early stages of a relationship is significantly reduced when the girl is the initial pursuer. So, I mean, if the OP wants to put the guy at ease...
posted by Juffo-Wup at 8:40 PM on May 4, 2012 [2 favorites]


Most of the time I ask a group if they want to do X and on several occasions he's the only one to say yes.

Maybe your tight-knit group of friends already sees the obvious attraction between you both (that is, if it exists, which it seems like it does) and always backs out when this happens so that you two can spend time together? Has it ever happened that you ask the group, this guy and a friend says yes, and then the friend has backed out?

Also, have you asked your friends? A third party who is also a close friend would probably be the first to know whether there's any mutual chemistry between you guys.
posted by suedehead at 1:25 AM on May 5, 2012 [2 favorites]


"I wouldn't pursue this until you resolve the resentment you feel at always being the initiator, because there's a very real possibility that's what you'd be signing up for."

That is a fair point. Though to clarify, in the past it was only one relationship where that bothered me. Another relationship that started where I initiated with a shy guy, once we were into the relationship, I was not always the one to start conversations or initiate intimacy. The relationship where I got irked about my role was one where the guy just couldn't be bothered to make the effort - even though I'd expressed what I wanted. He wasn't shy, he was passive and lazy. I think it is different when you're with someone who cares about your happiness, so if you express what you want or need they make an effort even if it is not comfortable. All of that said, point taken, and I might just continue showing obvious signs of being receptive and see what happens. That would be easier on my nerves.

"Also, have you asked your friends?"

Not exactly. One mutual friend is aware of my interest - I tend to be super-private about these things so wouldn't want everyone to know. This friend has said since he is shy, if I ask him out he'd probably appreciate it and say hell yes. She also asked if there was something going on between us, so I think the nonverbals are starting to get obvious with our closer friends.
posted by hungry hippo at 6:15 AM on May 5, 2012


Kiss him.

1. Do you think I am reading the signals right?

You won't know unless you kiss him.

2. I'm generally good at helping people feel comfortable, but is there anything else I can do to help my friend feel more at ease and less guarded about himself?

Yes, if you kiss him.

3. Asking shy guys (and others) for personal insight - If there is an existing friendship and fairly strong signals of romantic interest - would it put less pressure on a shy guy for a girl to ask him on "a date", or would it put less pressure on him for her to instead say something like she would not mind being kissed, leaving the labels and expectations of "dating" out of it? Also, would it be easier on a shy person to share this stuff in writing just before parting so they don't feel rushed to respond or would it be more appropriate to share when they could respond in the moment?

Shy people don't want to make the first move and will be happy if you just kiss them.

4. What are the practical considerations of a relationship between someone around 30 and someone around 40? How viable is it?

This could not be more standard a coupling. 30 and 40 are essentially the same age these days.

5. My interest in this person kind of caught me by surprise, and it is not so intense to make me feel crazy but I do think there is at least some portion of simple infatuation here. How can I make sure I make this decision based on the best interests of both parties, and not based on Spring fever?

Who cares? Just kiss him.
posted by Potomac Avenue at 7:20 AM on May 5, 2012 [3 favorites]


Kiss him... I've been thinking about that option. There are some logistical things to work out - it would work much more smoothly if he made that move due to me being shorter by a lot - but believe me, I haven't ruled that one out. :) Maybe I could grab him and pull him to me. And hope I don't seem like a creeper.
posted by hungry hippo at 7:26 AM on May 5, 2012


This is why the lord invented couches and movie nights.
posted by Potomac Avenue at 7:45 AM on May 5, 2012 [6 favorites]


I might just continue showing obvious signs of being receptive and see what happens. That would be easier on my nerves.

A great way to ensure nothing ever happening. If you are attracted to shy, hesitant, quiet guys, you may have to accept taking a greater role, or just watching them end up with other people who do.
posted by Miko at 7:57 AM on May 5, 2012 [2 favorites]


So I am playing with the following approach:

"Can you keep a secret?" [Wait for the "yes."]
"I keep wondering what would happen if I tried to kiss you."

Yay? Nay?
posted by hungry hippo at 8:04 AM on May 5, 2012


Fine! Go!
posted by thinkpiece at 8:13 AM on May 5, 2012 [3 favorites]


Oh dear. I might ask him to kiss him, but only if it seems like a good time to then execute said kissing. Do it. Start with touching his hand or his hair.

First, of all my short and long-term relationships, about 10 (I think?), I have only "officially" initiated maybe 1 or 2 of those, and those 2 were where it felt like we both knew it was the right thing to do.

I kid you not, I have sat on a girl's bed many many times with her until 4am thinking nothing more than "well she sure is a nice lady. I look forward to hanging out again. I should probably go to bed soon." And then eventually they kiss me or say something like "DUDE WHEN THE HELL ARE YOU GOING TO KISS ME?!?!?!"

That situation could be way more awkward if no one actually just goes for the kiss.

1. Do you think I am reading the signals right?

Yes! Definitely!

2. I'm generally good at helping people feel comfortable, but is there anything else I can do to help my friend feel more at ease and less guarded about himself?

Ask questions? Questions are easier to deal with than banter if someone is feeling shy. I am pretty shy and have worked hard at dealing with it. I have found asking questions or being asked questions really helps me feel less awkward. They don't have to be profound ones either. :)

3. Asking shy guys (and others) for personal insight - If there is an existing friendship and fairly strong signals of romantic interest - would it put less pressure on a shy guy for a girl to ask him on "a date", or would it put less pressure on him for her to instead say something like she would not mind being kissed, leaving the labels and expectations of "dating" out of it? Also, would it be easier on a shy person to share this stuff in writing just before parting so they don't feel rushed to respond or would it be more appropriate to share when they could respond in the moment?

Sending something in writing seems like it would require more thought and be way more serious than just trying to kiss someone.

4. What are the practical considerations of a relationship between someone around 30 and someone around 40? How viable is it?

Significantly less than if you were both 10 years younger. While people mature differently, a friend recently forbade me from dating any women under 25, her rationale being that ALL people at that age make many changes to their lives quickly. 30/40 seems much more stable.

5. My interest in this person kind of caught me by surprise, and it is not so intense to make me feel crazy but I do think there is at least some portion of simple infatuation here. How can I make sure I make this decision based on the best interests of both parties, and not based on Spring fever?


Do it! It is in the interest of both parties to get it on, or at least to try.
posted by MonsieurBon at 10:13 AM on May 5, 2012 [2 favorites]


Just kiss him! Putting him in a situation where he has to (or feels like he has to) verbally respond to the prospect of kissing or escalating your relationship might make him feel awkward. I am a shy person and have always felt awkward when I've felt I had to respond to questions/propositions in non body language or physical ways.

Good luck! I think you'll have success!
posted by ohmy at 10:15 AM on May 5, 2012 [1 favorite]


Smile. Eye contact. Light touching. Compliment.
posted by Ironmouth at 11:14 AM on May 5, 2012 [1 favorite]


There are some logistical things to work out - it would work much more smoothly if he made that move due to me being shorter by a lot -

Only if you are standing :) Get him sitting or lying and height won't be an issue.
posted by ersatz at 4:26 PM on May 5, 2012 [1 favorite]


I'm in a somewhat similar situation: involved with a guy (I'm a woman, so it's the reverse of your situation) who is both shy (as am I) and significantly younger than me. How we came to acknowledge the attraction to each other probably can't be replicated, but I'm here to say that you probably are reading the signals right, but they're harder to read in someone who is shy and/or not experienced. He may be ok waiting indefinitely for you to bring it up, so...bring it up! Good luck!
posted by FlyByDay at 6:28 PM on May 5, 2012 [2 favorites]


Thank you all for the wonderful answers. Happy to report it turned out to be a non-issue - I didn't have to say a word. Spring FTW!
posted by hungry hippo at 6:58 AM on May 6, 2012 [8 favorites]


Spring FTW!

Amen to that.
posted by Potomac Avenue at 2:12 PM on May 7, 2012 [1 favorite]


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