Late 20s adult woman suffering from teenage-like crush needs help
January 15, 2018 9:43 AM   Subscribe

This is really awkward and stupid, but I could use some help!

I met this guy randomly a few years ago and became friends with him, secretly harbouring a crush that I eventually revealed, I think, in a text message and he didn't feel the same (if I remember correctly). We got out of contact for a couple years. Then I was surfing around online dating last winter and noticed him and said Hi. We always had nice conversations so it was easy to talk to him. (He's just a genuinely sweet person, I think). Then we exchanged emails to keep in touch.
Randomly, he messaged me in the September to say he was back in town (he had been working in a different city for a few years) and asking me if I wanted to meet up. I remember getting a jolt when I saw that text, because I had really liked him before. But I didn't want to get attached again if he has no intention of dating me. So I did reply, but not right away, and didn't pay much attention. The next few months, we saw each other a few times, but I was so busy with work and other commitments, and was also casually dating someone else, and so I didn't think much of it at that time.

Then, after christmas, I found myself with a lot of free time. I'm off work and not dating anyone at the moment, and my closest friends seem to be really busy. And so I casually asked him to go out for food. So we went, and this time for some reason, he decided to pay . I think it was the first time he did that, but I'm not sure. Anyways, whatever.
Then randomly on a whim a few days ago, i invited him over to my apartment for beers. I didn't think it through, I was just bored, lonely and missed him. (Surprise, surprise, my crush never went away, unfortunately).

So we ended up talking for a few hours and then awkwardly making out and having sex and then lay around cuddling and talking for about 45 minutes, and then I was falling asleep so he went home (I stupidly have a single bed, lol). But we didn't really talk about anything related to our feelings for each other or whatever. I was ready to pretend it never happened and try not to freak out about it, but then he texted me 2 days later to ask me to hang out.

So then we went out on casual dinner and drinks date (he paid again). We decided to go hang out at my place again and watched a movie and fooled around, though I told him I didn't want to have sex because i wasn't feeling well (which he was fine with). Then I tried to be really sweet by walking him home and kissing him before we parted, which he seemed to like because he smiled.

When is the appropriate time to ask him whether he wants to have a real relationship or if it's just casual to him? I am dealing with a lot of paranoid thoughts about this that I could help sorting through. 1) he is only interested in me because I am an easy target that liked him in the past. 2) He actualy finds me annoying. 3) He is way too cool for me and always will be. 4) he's not the type to commit to anything so it's pointless.

So it's clear that I have him on a pedestal right now because of that secret crush I had buried, but I think underneath that is a genuine admiration for him. How can I tap into that real feeling when i'm swarmed with all these anxieties that make me act really weird around him?
How do I manage this situation in which my "fantasy" came true but I'm not sure what that actually means in the real situation I'm in? How do I get him to get off the pedestal but also not get my heart broken again? Or should I just risk getting it broken because then at least I tried?
posted by winterportage to Human Relations (7 answers total)
Re: your paranoid thoughts, you have no idea if any of those are true. They could be just as easily true as 1) he's interested in you for you 2) he finds you cool 3) he thinks you're way too cool for him 4) he wants to get married and have babies. You know?

First, be clear on what you want generally. Are you looking for something serious at this point in your life? Or do you want something casual? And what do you want with him specifically?

Having that in mind, next time you see him, open up the conversation. Ask him: "what are you looking for?" Tell him what you want: "I'm looking for something [serious/not serious]. I'd like to explore our connection further..." And then go from there.

To get him off the pedestal: think about what you want in a partner and relationship and see if he meets those. You guys have some history and right now he's sweet and cool but how well do you really know him?
posted by foxjacket at 10:03 AM on January 15, 2018

When is the appropriate time to ask him whether he wants to have a real relationship or if it's just casual to him?

I think it would be okay to say now "Hey, we've been having fun together. I like you. Before we go further I'd like to make sure we're on the same page. I'm looking for xx. What are you looking for?"

It's okay - and sensible - if neither of you is ready to commit to a serious relationship right now as you're still getting to know each other, but if he's looking for something casual and you're not, better to cut your losses.

Good luck!
posted by bunderful at 10:37 AM on January 15, 2018 [3 favorites]

well, your paranoid fears are incompatible with him being a genuinely sweet person. A sweet person would never use you just for casual fun without making sure first that it wouldn't hurt you, and would never sleep with someone he's too cool for, would never repeatedly date someone he found annoying. so let's say that if he's the person you think he is, the very worst you could find out is that he likes you but isn't ready for as serious a relationship as you are. and then you can tell him no thank you. try not to scare yourself with anything worse.

When is the appropriate time to ask him whether he wants to have a real relationship or if it's just casual to him?

Whenever you need to know, which sounds like now.

Paying for dinner is the inarticulate boy way of saying you're not just friends who sleep together, you're really Dating, right? for young men who are just as afraid to initiate this conversation as you are? I hate that shit but I think that is what it means. so let that give you some confidence as you prepare to talk to him. If you seriously don't remember for sure what exactly you told him via text a few years ago and what he said back, then he probably doesn't remember either. And it may not have been clear to him at the time how serious you were. so, tell him you really like him as if it's the first time you're telling him. and that you've known each other long enough that you know you want this to be the beginning of something serious, not an indefinite casual time-waster.

you don't have to plan out a whole position statement, you should know pretty soon after you start talking how he feels. either he will be very happy and agree with you, or he will start to get uncomfortable and start talking in circles about how he likes things to evolve organically and doesn't want to put labels on things and you're really great but it's too soon for commitment and. If you hadn't known him on and off for years, it might be too soon, but you have, so it's not.
posted by queenofbithynia at 10:44 AM on January 15, 2018 [2 favorites]

One of the risks of dating is that one of you may be really into the other and it's not reciprocated, so there's no 100% sure way to protect your heart from that scenario. However, it seems like the two of you are doing okay in a casual sort of way right now, so I'd say to keep things light, keep seeing him and try to enjoy the times together for what they are, not as much as what you felt in the past or you think he thinks about you, if that makes sense.
posted by xingcat at 10:45 AM on January 15, 2018

When is the appropriate time to ask him whether he wants to have a real relationship or if it's just casual to him?
Now is fine, but I don't think that it will tell you the answers to your questions (or at least, his answer is not necessarily a guarantee that these things aren't true). The only way is to see him, talk to him, observe.
posted by sm1tten at 11:27 AM on January 15, 2018

The sequence of recent events so far sounds like an ideal casual dating situation. That said, many men I've met in the late twenties-to-mid-thirties age recently prefer not to have "serious" relationship talks early in the dating timeline. And you've technically only been on one date, so it is still really 'early.'

That said, I think you could get an idea of how he feels by letting him know you'd like to be exclusive. Your own feelings notwithstanding, sleeping with someone entails a certain amount of risk to yourself, and framing the question that way could relieve some of the pressure of a 'relationship' talk. It's also a good lead-in to it.

Also, is his online dating profile still up?
posted by Everydayville at 11:42 AM on January 15, 2018 [1 favorite]

I think the way you get him off a (comparative) pedestal is by elevating the respect you give to your own needs. So maybe try something like, "hey, this has been really fun, I'm really enjoying it. I feel like you're someone I could really be into if i let myself. And I'm not really looking for a Friends With Benefits kind of thing. What about you?" How he reacts will tell you a lot. Again, getting him off the pedestal is about not accepting whatever scraps he's willing to toss down just so you can gaze at his feet; it's about respecting yourself (and him) as equals and setting the terms under which you'll engage.
posted by salvia at 12:48 PM on January 15, 2018 [16 favorites]

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