TLDR: I’ve been into this guy for close to a year now, basically since the day we met, and it seemed as though he was into me too, but shit always seemed to get in the way of us ever becoming or doing anything. Seemed like it might finally happen this time around as we’ve been very flirtatious since coming back to law school (something many of our friends have picked up on, so I don’t think I’m reading into it too much), but I just found out he’s seeing someone. I’m feeling really confused and, perhaps unreasonably, a bit led on, but I’m trying to figure out the best way to continue so we maintain our friendship while also protecting both of our interests and feelings. Basically the main thing I’m trying to decide is whether and how to address the elephant in the room or to let it be and try to just move on.

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(Very) long version here:

I met this friend (we’ll call him M) when I was in the midst of a pretty tumultuous relationship/situationship. I was definitely into M, but obviously nothing was going to happen because of the relationship. Still, every one of our interactions felt very flirtatious, and the more time I spent with him, the more I felt as though we were becoming very close and acting pretty interested in one another for two people who weren’t planning on dating/hooking up/anything like that.

The relationship finally ended a few months into knowing M, shortly before the end of the semester (we’re both law students). He invited me to smoke with him at his place alone the night after finals concluded, which I took as kind of a proposition, but his dealer fell through and I got caught up doing something else so we didn’t end up hanging out. I tried making a bit of a move later that night by putting my hand on his leg while we were drunk in a friend’s car on the way to the end of year party, but he didn’t really do anything to reciprocate, so I decided to just let it rock and play it cool. I didn’t know if he wasn’t reciprocating because he wasn’t interested or because we were drunk or because he wasn’t totally sure of my relationship status, but by the end of the night we had separated: he was knee deep in taking care of a drunk friend while I ended up going home with someone else.

Fast forward, the summer’s gone by, we get back to town and he’s the first person I see along with the rest of our dungeons and dragons group. The conversation is very flirty, as usual. A few nights later at a party we spent the entire evening talking and he even suggested he come over to my new place once I’m fully moved in to hang out, which again felt like somewhat of a proposition. Cool, this is good.

A week later we’re at another party and talking. My plan was to hopefully hook-up/make out/set something more concrete in motion after this party, but I also had already made the move on M before the summer that wasn’t reciprocated, and I didn’t want to violate his boundaries by trying something again, so I decided to leave the ball in his court. We’re standing there talking and a friend comes by and drunkenly asks “when are you guys gonna fuck already?” M is visibly upset and walks away from us without another word. I see him later that night talking to a girl I’d never seen him interact with before, and it clicked: there’s probably something going on between them, that’s why the comment made him so uncomfortable and why he hasn’t initiated anything.

Later in the week I learn from a mutual friend that he recently started seeing someone, but very much on the DL. Still, the same day I learn this information, he’s being very flirty with me in every conversation—making lots of eye contact, sitting very close to me, laughing at my jokes, showing me his fucking Pokémon that he named because I told him a few days earlier it was lame not to name your Pokémon. Like, it really feels like he’s still coming onto me even though I just learned he’s seeing someone.

So now I’m confused. M still hasn’t told me anything about this new relationship despite us being pretty close, but it’s clear something is happening. We’ve still hung out multiple times over the past few days as we have a lot of mutual friends and often end up at social things together, but he’s been noticeably kind of avoidant. Still though, friends of mine are asking me when he’s going to finally ask me out because everyone around us seems to think he’s interested in me despite him currently seeing someone on the DL. It feels almost as though he’s using me, even though I don’t think he would do that — at least not intentionally.

So, I guess I’m trying to figure out what the appropriate thing to do is. I want M to be happy and to explore this relationship if that will make him happy. But if he’s seeing someone else, I don’t think I can take the consistent flirty behavior as it makes me feel confused and feels somewhat disrespectful to this girl he’s been seeing and to me. (I say this being fully aware that I flirted with him while I was seeing someone, and that definitely wasn’t okay and probably confused him. So maybe this is what I deserve, who knows.) But I also don’t want what he’s been doing the past few days where he acts shifty and avoidant around me as though I’m a ticking timebomb. I just want to know 1. What the hell is/was going on between us and if I was wrong for thinking he was coming onto me, 2. What the situation is now and what he wants/needs from our friendship, and 3. What steps to take to move forward in a way that lets our friendship continue, protects my feelings from getting hurt, and allows him to live his life and explore this relationship if that’s what he wants.

So, what do I do? Do I confront M about the flirty behavior while he’s secretly seeing someone he hasn’t told me about? Do I ask him to stop the flirtatiousness so we can remain friends? Do I tell him I have feelings for him? Or do I let it all just pass without saying anything at the potential expense of my feelings but perhaps to the salvation of our friendship?

2 comments
  1. 1. Sometimes people are just flirty. And to be honest, if I were in his shoes, what I figure is that if things don’t move quickly to a relationship (which this didn’t) that the window of opportunity closed, its over, the end, get over it and go out with somebody else.
    2. That’s something only you and he can answer.
    3. If you’re feeling hurt, spend less time with him. Don’t have to fully cut him off but it’ll give him more time with his new squeeze anyway. I have a whole thing about getting over crushes on friends, and step 1 is to identify friends who *aren’t* mutual friends with him – like friends from undergrad or HS who’ve never met him, and just vent your feelings at them. Keep the blast radius going *away* from him. Then give yourself a project, I find fitness projects work well but no reason it couldn’t be learning origami or perfecting a bread recipe. Something distracting.

    Don’t confront him, there’s no betrayal here cuz there wasn’t any agreement. Its fine to just simply say “hey can you be a little less flirty with me it makes me a little uncomfortable.” Simple enough. No need for him to know about any romantic feelings, that’s just going to make both of your lives harder. Just let it go.

  2. I would let it blow over or just tell him what you think and feel. Might sound dumb but he might of been unsure how you felt as well and thought the flirting was part of the friendship dynamic. He also might genuinely like you but was nervous about making a move and loosing you as a friend if it didn’t work out.

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