How do I figure out if I want to date my friend when I've never flirted?
October 29, 2017 6:48 PM   Subscribe

Also I don't really want him to know I'm attracted to him in that way, before I figure this out. Also we are both awkward pandas. Way too many snowflake-y details inside. Ugh.

I'm sorry this is so long. This really should not be that complicated and yet it feels insurmountable to me.

I am a cis het woman/non-white/child of immigrants. He is a cis het man, white; let's call him X. We've been casual friends for ~1 year translating into periodic/casual hangouts (basically meal & movie theatre & yakking about stuff before & after).

We are both in our 30's and live in the same city. We both grew up and have mostly lived in somewhat rural America (the city where we live now is pop. ~200,000, and a veritable metropolis compared to the rest of the state). Neither of us would move away unless we had very serious reason to; we're both currently pleased living here. He's traveled and lived abroad some; I've only vacationed out of the country a couple times. He has a proper career in tech, and I have a job that suits me well because I leave it behind when I clock out each day.

X and I are both really independent. He's reserved and a homebody in his daily life, in much the same way I am, only a fair bit more so. We are in the same friend group and are the only single people: he knows most of them through work but socializes with them outside of work; I know most of them from teenagerhood and am quite close/very close to most of them in general. I suspect he doesn't just have a dislike of crowds of people but might have a bit of anxiety about it based on what he's said in passing and what I've observed. He seems totally fine at dinner parties and gatherings of that nature, if quite a bit more quiet than when he's one on one with someone (like with me).

In his spare time, he likes doing solo projects like building stuff from scratch, carpentry, house projects/improvement, etc. Alas, I am 100% useless at that stuff. :( I think he also might be moderately outdoorsy (also not my forte). I live in my head a lot, and like to tell people my hobbies are art appreciation (read all the books! watch all the movies! listen to all the music! + in all the ways possible, of all types under the sun YAY!, daydreaming, going to cultural/literary/community events by myself or with a willing friend or two) and friend appreciation (which these days is meeting for a meal or coffee or a walk in the park or tagging along with friends on a kid-friendly thing with their kids in tow and me getting to be the cool, fun auntie in the group).

That all sounds like I am some social butterfly but I really am not at all. I like attending things alone because for me there's no pressure to socialize with people I don't know if I just don't feel like it, and I can slip away if it's too much for any reason. I REALLY value my alone time/recharging time, and have been known to go 3-5 days without communication with other human beings beyond work hours, and mayyyyybe a phone text or three. Having that control over my alone time/recharging time makes me also enjoy my time with people I love and care about so much more, if that makes sense.

I get the impression that X and I are very similar in this respect, and that our respective living quarters are our sacred "alone" spaces.

I've struggled with clinical depression and some mild anxiety that manifests under certain circumstances for most of my life (+suicidal ideation for 2 longish periods; never attempted), but with meds, I've been doing quite well for about 3 years. I like how my life is right now, and look upon the space to grow with a optimistic, hopeful attitude (creative writing, being a more active participant in community/social justice stuff).

The only time I caught romantic feelings for someone in my adult life was years ago and I came here for help at the beginning of that dark (i.e.! supremely!! annoying!!!) time in my life. It was awful for me for almost 2 years (I KNOW) because I was a terrible communicator. When we finally had a conversation directly addressing my attraction where I told him I wanted something more, everything resolved quickly and neatly. The resolution was not negative at all beyond a brief period of combined exasperation at myself/embarrassment on my part; in fact, we became much better friends afterwards and remain so to this day.

I have ZERO romantic/sexual experience. I'm not just a virgin & have never kissed anyone, I've never even flirted. My inevitable response to my schoolgirl crushes was to notice + ignore utterly + pine in agony from afar. Once, a boy I liked said to me, "I think you're hot" in a serious voice, and I said "thank you," thinking he was joking because I had no idea what to do if he wasn't, and then I never spoke to him again (though I continued to pine). I've been asked for my phone number once or twice in college and I just brushed the requests off. I am notorious among my friends for being oblivious to men flirting with me unless it's well beyond flirting and into harassment territory (the rare ass grab, inappropriate sexual comments from strangers). I'm only made aware of flirting having happened in my specific direction when friends tell me that yes, it happened, upon which my reaction is zero to negative interest re: follow through.

The closest thing I can think of me deliberately flirting is one time a decade ago, when I "accidentally" on purpose touched knees/brushed hands with a devastatingly handsome new friend I'd just met. That didn't go anywhere and I doubt I wanted it to, but it was fun & exciting to do that on purpose and get a mildly positive response for 5 minutes.

I found it easy as a young girl to follow my parents' old-fashioned rules about being ladylike and how to conduct myself around males, and was happy to never date or fool around when I was in high school. But it would have been equally easy for me to push back against those same rules; my sister rebelled against those rules and made sure our parents knew it; she did what she liked in that regard (tame/ordinary teen stuff), and no long-standing drama ever happened as a result. My relationship with my parents has been rocky in the past (having to do with my mental health struggles) but we get along great now and I visit them 2-3 times a month. They don't pressure me at all about dating or getting married as I've made it clear to them I don't welcome that from them. Culturally speaking, this is a bit unusual among THEIR friend group, especially with a daughter my age. I'm particularly grateful for their respect on this point, honestly.

So I thought I had figured out last year that I am asexual. I was so pleased to finally solve the puzzle of why all my life I've had such a large personal bubble (physically) and am so content being in it when I don't have any trauma or abuse in my past. I also attributed my overall obliviousness and lifelong near total lack of sexual interest/curiosity to my apparent asexuality.

I realized a month ago quite suddenly that I've caught feelings for X. My reaction was: Oh for fuck's sake UGH (not a disgusted UGH, but a this-nonsense-is-annoying UGH).

It's just a crush. But it's a thing that I should do something about, because I'm randomly daydreaming about how kind his face is, and thinking about ways to get him to go do a wider range of stuff with me more frequently than we've been doing. And I find this uncertain pining extremely bothersome!! Thus, I want to do something about it so that the pining actually clarifies itself towards one direction or another.

However, what I don't want to do is signal to him anything about my attraction until I know whether or not I really would want to move forward with anything romantic at all. This is because I think it would be shitty of me to say, "Guess what, I just want you to know I dream about your stupid long eyelashes now but haha, I don't know if I want to actually DATE YOU. Maybe let's just make out. I've not done that before by the way and might not at all be into that once we get going because I think I might be mostly ace! What do you think!" For some people, this would not at all be a big deal, and perhaps the best course of action. For X and I, if I say something to that effect, it would result in awkwardness for a long while, if he felt the same way or didn't, and I wouldn't put it past me or him or BOTH of us to avoid contact in order to deal, and, uhhhhh, thinking about that possible outcome makes me rather sad actually. A tangled mess lies down that path.

What the fuck do I do? The barrier I'm coming up against is that I want to get to know him better, WITHOUT signalling to him that I'm attracted. I'm basically vetting him for dating, apparently, but I want to maintain/deepen our friendship first (at the same time??!) because I enjoy his company overall. The only thing I can think of is just constantly inviting him to do stuff with me so we can spend more time together, which will be tricky because the things I like to do sometimes necessitate going out amongst crowds, which he has already told me he tends to avoid. And I don't get the impression that he's a big reader (books and films are how I most easily and quickly connect with people), so anything remotely literary is probably out. I thought I could invite him to my house to hang out and watch a movie, but isn't that exactly what Netflix and chill means, i.e. getting busy? I even batted around the idea of blatantly inviting myself over to HIS house to check out the latest project he's working on. But that feels invasive (see above re sacred alone space!) because he's never invited me himself though he always tells me about what he's working on when we're together. And I can't make the excuse of offering help or sharing expertise or knowledge because he knows I'm bad at that stuff.

Further low-key complicating this is that in our circle of friends, everyone knows that "Phonebia values her independence and has no interest in dating and is perfectly happy being single" and I actually ... don't want to dispel this view of me.

Because I am entertaining the idea of ONLY dating X. Entertaining the idea with absolutely any other person right now sounds like a Huge Drag That I Do Not Want to Be Bothered With.


1) Tell me what to do in step form. I just have no confidence in my ability to not mess this up without it turning out badly for our friendship.

2) ... Straights, is it even possible to actively try to spend more time with someone of the opposite sex without them suspecting you're attracted to them, when they will probably figure out that this increased invitation rate is clearly out of the norm for you based what they've gleaned from our past interactions and what they know about me from mutual friends? :(

3) Follow up on #2: Is doing this (vetting a friend to see if you want to date them) even with thoughtful & respectful intent going to just come across as "playing games" and result in confusion and hurt feelings? Because I do absolutely do not want to do that.

4) I realize a large part of the problem is not just fear of having our (already casual but I want it to be better!) friendship suffer or cool because of me not handling this correctly, but also me just being scared of rejection. I don't really know how to overcome that, but to be clear, I want wiley action items, I'm not asking for advice on how to overcome the fear of rejection. (Unless that's literally the only action item possible to avoid wasting away from Useless and Annoying Pining Disease. I don't know! I don't know how any of this works! See #1!!!)
posted by phonebia to Human Relations (21 answers total) 3 users marked this as a favorite
I'm sure someone else will give a more in-depth answer, and admittedly crushes ARE had and stressful, but you seem to have a lot of social anxiety and I'd really, really strongly encourage you to address this. It's still a problem even if you only have anxiety around romantic experiences. It doesn't have to be this hard. Cognitive behavioral therapy is short term and has been proven to be effecive for social anxiety in particular.

I don't mean to derail; it just seemed like there was a LOT of anxiety in your post. We can help you with the particulars of this situation, but we cannot help you with the anxieties underlying the problem in general. We can give you step-by-step directions here but you'll be far better off getting the tools to handle this yourself now and in the future, tools you can generalize should this ever come up again (which it probably will, in all honesty).

With that said: take a deep breath. It's okay to talk to him and get to know him more. These aren't feelings to be afraid of and you don't need to hide your interest. It's not shameful. Just try talking to him more.
posted by Amy93 at 7:03 PM on October 29, 2017 [2 favorites]

You are not as snowflakey as you think you are. This whole "dating" thing mostly only happens in the movies and on dating apps (when the intersection is not explicitly a transitory hookup.) I think a lot of people basically hang out together over time and then someone kisses someone (or doesn't.) That's exactly what you're talking about: hanging out to develop a deeper sense of how you like him. It is the opposite of playing games.

Flirting is not required; there are many people who just use their words instead of their eyelashes or whatever.

So I would go with "constantly inviting him to do stuff" which is a thing that even friends do so could just result in ramping up your friendship with him. But it will give you scope to spend more time and figure out if you actually want to smush your face into his face.
posted by DarlingBri at 7:29 PM on October 29, 2017 [8 favorites]

People go on dates to decide if they want to get into a relationship. Pre-dates are not necessary.

You should ask him out on a date. You can hedge if you want; say "hey, we're the only single people in our social circle, do you think we should try going on a date?" or "Do you want to go out to dinner? Yes? Cool! Is this potentially a date, or just a friend thing?" You don't have to give away the intensity of your interest when you ask him out, or say a single thing about your lack of experience.

I know it's still scary. But I also know it's more likely to get you what you want than dancing around it. And if he says he's not interested you can have a line in your back pocket to respond with; "I get it, no worries, but I'd still enjoy hanging out platonically" or the like, so you don't freeze and feel even more awkward.

Dating means leaving yourself a little vulnerable. It's tough, and I know why you want to avoid it,but there is no way to escape it completely. If it helps, know that most people find it scary and are terrified of rejection; they've just gotten more used to it than you have!
posted by metasarah at 7:31 PM on October 29, 2017 [8 favorites]

Because this guy has said he's not a fan of crowds it sounds like it would be easy and kind of you to invite him to do some things that are date-like in structure because they're inherently just for two people. Like meals, seeing a movie or performance, going on a scenic drive to appreciate a view, etc. It might be that he doesn't do a lot of "art appreciation" stuff because that can be a big group thing when it's not a date, and he's not dating anyone. So my suggestion is to invite him to do one-on-one things, no flirting or romantic intentions involved. This will let you know if he also wants to spend some more time with just you, and give you a chance to know him better. If he wants to spend time with you and you've already done the work of planning and inviting him, he'll brave a crowd or two as long as the destination is calm.
posted by Mizu at 7:43 PM on October 29, 2017 [1 favorite]

1) It doesn't sound like you're asexual, rather that the pool of people you find attractive is fairly limited so most don't awaken these feeling in you until
2) you met someone you like! Awesome. It doesn't have to be a major anxiety inducing deal, though. Instead of considering it a proper date, just invite him to, you know, hang out occasionally and see if you like him enough to maybe do it again. Coffee is fine. Going to see some art or (insert activity he likes) is great too. Then you have something to talk about.
3) once you spend some time with him, you'll get a better idea of how you feel. And don't tell anyone, but that's all that dating is!
posted by Jubey at 7:54 PM on October 29, 2017 [1 favorite]

I think you should just find ways to spend time alone with him, and if that turns into evening and late-night conversations and both of you are excited to spend time with each other and maybe you guys go out for drinks to loosen up then maybe you'll realize you do like each other and make out. But you don't need to call anything a date if that feels like a lot of pressure. You can just hang out together.
posted by ball00000ns at 8:53 PM on October 29, 2017

Thank you for all the great answers so far! Lots to think about; particularly the observation about anxiety from Amy93.

I should also mention that I don't want a repeat of my previous experience, i.e. failing to communicate effectively and thereby letting something drag on & cause me easily avoidable heartache for a ridiculous amount of time (2. Years.)

So with that in mind, at the risk of sounding like I'm putting the cart before the horse is even born:

In the event that I decide upon the method where I just invite him to do more stuff with me, I would just invite him along to whatever I was already planning on doing as long as it wasn't obviously a thing he would very likely avoid (like a concert of a popular band) and it would just be him and me. I would resolve not to worry too terribly about whether or not he would be interested enough in the thing because I already know that I would carefully and methodically talk myself out of inviting him in the first place altogether.

A FORESEEABLE PROBLEM: But how many times do I do that before I stop with this frequency of inviting him to join me to do whatever (3-5 rejections in a row to things we haven't done/attended together previously?)? and/or over what period of time (2, 3, more months, with more nah's than ok's? My max is 6 months, and that already sounds really, really stressful)? What I mean is, is there a general guideline I can use to know when to stop extra-inviting him to stuff and revert back to the current status quo of occasional meal/movie?

I'm asking because if he is not interested in me in that way and does not see any potential for more than what we've got now, I don't want to suddenly become The Annoying Friend Who Won't Stop Bothering Him with Invites to Stuff He is Not Interested In and Is Constantly Putting Him in the Position of Saying No. Because, again, I'd like to preserve our friendship as it is if it's not possible to have anything more, and I would imagine being The Annoying Friend for a prolonged period of time would damage that.
posted by phonebia at 10:28 PM on October 29, 2017

(And please don't say, "he'll figure out your intentions by your change in behavior."

As mentioned above, I am pretty goddamned oblivious and want to extend equal benefit of the doubt. Ok, done threadsitting now. Thank you guys so much.)
posted by phonebia at 10:34 PM on October 29, 2017

You've been friends for a year, give yourself a year to try taking it to the next level. Give yourself room to take it slow, but give it a deadline.
posted by rhizome at 11:03 PM on October 29, 2017

If you're both single and you've been hanging out in a close way for awhile, and neither of you has expressly disclaimed being attracted to the other, I'd give there a better than 50% chance that this goes both ways. Not 100%, but better than even. If he';s not attracted to you and you do this now, there's still a chance that you can go back to being just friends. (Have done so! Still friends with the person a decade and change later!) If you wait another year to actually put it out there in plain language, you have one more whole year worth of emotional investment in it, and you drastically decrease the chances that you can make it through the fallout. Holding onto these things without actually spelling them out seems lower-risk, but it isn't. Yes, it's potentially awkward--but so is hanging out with someone you have feelings for. Rejection is awkward. So is dating. Everything here is probably going to be awkward! Stop deciding based on trying to second-guess comparative levels of awkward, and just get something said that can't be misinterpreted by another awkward person.
posted by Sequence at 1:33 AM on October 30, 2017 [3 favorites]

My general rule of thumb is that if someone declines 3 invitations without reciprocation or without making it clear that they appreciate the invitation and would like to do something together, I drop it.

If you go the route of inviting him to do more stuff with you and after 3-5 events you still want to date, go ahead and bring it up.

I agree with Amy93 that seeing a therapist would probably be helpful. You might be interested in this article on avoidance and anxiety.

Note: I also have trouble with not wanting people to know I like them, but do you know where that gets you? Nowhere. It gets you watching Netflix on a Friday night and wondering what your crush is up to, and learning that they've started dating someone else while you were subtly angling (or just waiting) to get to know them a little better.
posted by bunderful at 5:52 AM on October 30, 2017

There’s really nothing special about the whole story. Since you like the man, ask him out on a date.

If that proves too much, then address your discomfort in therapy.

I’m sorry you’re feeling that way but very little justifies the wall of text with you dissecting every single thought (confession: I’ve skipped half of it)
posted by Kwadeng at 6:06 AM on October 30, 2017 [8 favorites]

Can you think of a project that needs doing in your house? A shelf that needs installing? A dimmer switch or light fixture? Art that needs to hang evenly? You could invite him over to help you because he is handy and you are not, and you buy him dinner afterwards as thanks.
posted by xo at 6:21 AM on October 30, 2017 [2 favorites]

I've got social anxiety and the absolute best way to get over the over thinking it is to just do whatever it is. The longer I obsess over it, the longer my brain weasels play keep-away with the idea of it, the less likely I am to make a decision and take action.

Ask X on a date. The sooner the better.

(also, my therapist has totally helped me work on my social anxiety, so I'd also recommend that!)
posted by carrioncomfort at 6:53 AM on October 30, 2017 [2 favorites]

I would hit Pause on this current situation, and practice flirting and dating. Decide if you want to be the one to chase men or to signal them to come to you. Watch the movie "Duty Dating" on youtube. Practice flirting- eye contact and a smile x 5 seconds. That's all it takes. Accept all invitations for a date whether you find them attractive or not, and go out with a few people at a time. You'll come away with some more confidence and less anxiety.
Then use your practice and flirt with him. If you want to be chased, talk about the things you're interested in doing or seeing without inviting him. Wait for him to ask you for a date. If you're sending signals and he's not responsive to it, it may be that he isn't interested.
posted by kwren at 8:02 AM on October 30, 2017 [1 favorite]

I think it is important that you do this in a way that respects your own way of being in the world. So, yes move out of your comfort zone and see if something happens but don't try to fake flirting and teasing if that isn't your thing.

My suggestion -
Ask him to do things, just the two of you, that you think you would both enjoy. Don't call it a date. If he asks you if it is a date say "I don't know. I don't usually do dates but I would be definitely interested in making this a date if you wanted to"
If you ask him twice and he gives vague excuses, you can probably take that as a no. You also have the option of actually saying, "I don't want to be a bother. If this isn't the kind of thing you would be interested in, just let me know and I'll stop asking". Anything other than active enthusiasm for being asked again should be taken as no.
If you ask him a couple of times and it seems like he is interested but says no, then ask him to propose the next possibility or to call you when he has more time.

When you feel like you are ready to move from friends to romance, it is really OK to use words and see if he is interested instead of just leaning over at some mysteriously magical moment and trying to kiss him. I know they don't it that way in the movies but there is nothing wrong with actually asking someone if they are interested instead of just imposing on them and forcing an awkward moment if they weren't. Plus, if this is going to work, because of your oblivious thing, you need a partner who can be both gentle and blunt at the same time. If he has a problem with you asking for clarity, he's not the right guy for you and that's an OK thing to find out.
posted by metahawk at 9:45 AM on October 30, 2017

I generally think three is the magic number here. If he declines three times and doesn't make alternative suggestions, I'd let it go.
posted by DarlingBri at 10:16 AM on October 30, 2017

To be honest, I think the straightforward approach would be best in this situation. I'm a bit like you in that I feel a lot better about an awkward situation once it's all out in the open, and he doesn't sound like the kind of person who is going to get any subtle hints.

1. Try being a bit more physical with him when you are together. Sit closer to him. Touch his arm to get his attention or bump into him when you're walking. How does that make you feel? Does he reciprocate at all?
2. If you like how it makes you feel, and he doesn't seem repulsed, tell him everything you told us (but edited down for clarity), either in person or by email.
3. Make it clear that whatever happens, you still want to be friends.
4. See what he says.
5a. If he says he's interested, talk about what sort of intimacy you'd like to try and see how it goes.
5b. If he's not interested, and you really do still want to be friends, try to spend some time together sooner rather than later, so you don't let the awkwardness develop too much. Jut be like, "ha ha this is awkward but that's okay, let's just go see that completely nonsexual movie and eat tacos"
posted by exceptinsects at 10:47 AM on October 30, 2017

1) Tell me what to do in step form.
Here's some suggestions that are more specific, but certainly not exhaustative:

When he talks about his projects, show interest enough to ask whether you might be able to see what he's talking about. This way, you could get an invitation (on a completely friendly basis) to his place to see what he likes to do.
While there, show more interest in either specific things to do with i) the project, ii) how he comes up with his ideas, iii) what difficulties he encounters and how he works through them, iv)lead into making comments about things that you like or find interesting about his home environment, v) share something personal about yourself (possibly about your home environment that might shed some light on your quirkiness) that you think he may not know and to which he could possibly relate... or not... if you feel safe in doing so without being judged or overly vulnerable.

Lastly, determine his response. ie: does he share his passion for his work with you after you encourage him?, does he offer support or encourage you to share more of your thoughts and feelings with him when you throw him a crumb (speaking metaphorically here)?, does he smile and make eye contact with you a little longer than you might expect a platonic relationship?, does he open up at the gentle probing into the personal, or does he shut down and drop the subject? These are all signs that you can watch for before stating any particular interest.
And do you actually like the attention he gives you? That is important, too.

Or just tell him that you have a crush on him, and see if that evokes a response... but drop it completely if he seems uncomfortable about the idea. It could take a few days or longer for that to sink in, but still, at least you'd start by being honest with him, and yourself. A "crush" doesn't mean that you need to "date" or take things romantically. It just means that you like him. It's flattering for most people. It may evoke an honest response from him and you could learn that he has a much more complicated life than you realize, or not. At least you'd learn something.

2) ... Straights, is it even possible to actively try to spend more time with someone of the opposite sex without them suspecting you're attracted to them

Absolutely! ... but if someone believes that you are simply happy on your own, they could simply ignore their own feelings of desire out of respect for what is believed to be your personal preference, and then a pattern of respectful distance could become locked in - and you may end up watching that person go on to find romance elsewhere, because you never expressed your interest.

3) Follow up on #2: Is doing this (vetting a friend to see if you want to date them) even with thoughtful & respectful intent going to just come across as "playing games" and result in confusion and hurt feelings?

Dating does not mean exclusion of all others to the point of being each individual's only means of getting social and supportive needs met. Dating is a way of learning more about each other to see if the two of you are a good fit. Mutual exclusion could be something that comes at a later date, or not, depending upon the circumstances or preferences of either person.

4) I realize a large part of the problem is not just fear of having our (already casual ***but I want it to be better!***) friendship suffer or cool because of me not handling this correctly, but also me just being scared of rejection.

I highlighted your statement in bold above, just to make you more aware that this is what you have already realized to be your TRUTH. If anything, be honest with yourself, express your truth, and be open to the way things unfold. I also worded it this way, because that way, you can truly see if anything develops.
Don't force intimacy that isn't forthcoming, but make it known how you feel - even if it means stating that you really don't know how you feel about the situation... and let things unfold.
It may blossom like a flower opening from a bud, or it may go dormant for a while and possibly turn into something different altogether, which could be altogether more appealing!
You just never know unless you express your truth! That is your pining more than anything else. It is the pining to express what you are feeling.
Emotions are just that: energy- in motion. It is what makes us alive and thrive. I hope you allow yourself that freedom.
posted by itsflyable at 2:40 PM on October 30, 2017 [1 favorite]

You figure out if you want to date someone by going on a date with them. If you both like it, then you go on another.

It's like the lottery. You can't win if you never even buy a ticket.

Ask him out. You don't have to try to be flirty or sexy ot suave or cool. "Wanna go do X with me, like as a date?"
posted by Green Eyed Monster at 6:49 PM on October 30, 2017

I simply asked in a text if he’d like to go on a date with me. He said he’s not looking to date right now. And I said, all right! Boom, all done, everything is normal. Thanks, everyone; you guys gave me a lot to think about and consider.

Conclusion: The straight forward inquiry was fastest and afforded me the least amount of angst.
posted by phonebia at 5:42 AM on November 15, 2017 [5 favorites]

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