Hello! So…this story is long and a bit messy, at least in my eyes. I’m not very good at summarizing information but I’ll do my best. I apologize beforehand for the lengthy post!

Shortly put, this is about a man I met though a guy who has been, bluntly put, my f**k buddy for about 4 years. I won’t go into details about that relationship. I’ll just say I’m not emotionally attached to him and decided to enjoy the relationship for what it was, while at the same time using it as an opportunity to practice having relationships that aren’t 100% intense, since I have trouble in that regards (I tend to think of “true” friendships as very intense relationships).

I’m at a point in my life (just graduated fromc collage) where I’m not getting my social needs met by my old group of friends, so I’ve started to see value in having some not-so-close friends with whom I can hang out and have fun. In this line of thinking, I decided my friend with benefits could be a gateway to a more active social life. Did it work? Well, sort of. He has invited me some times to party at his house or hang out with friends (always in the context of we having sex afterwards, though) and these times nothing really came out of it, meaning I didn’t really meet new people, with whom I continued to be in touch.

Last time he invited me to a party at his house, however, about a month ago, I met, and eventually hooked up (whoops), with one of his friends (let’s call him B). I had a good time, I was really interested in him (which doesn’t usually happen), he seemed genuinely interested in me, and I ended up staying until 4-5 pm at his house, hanging out. He said he’d had fun, mentioned some plans he had that afternoon at a place that was really close to his house; mentioned the weather was nice and that it would be nice to go to the park, etc. All this time I was wondering: is he just saying this to be polite? Is he inviting me? Is he hinting he wants me to go with him? Am I overstaying? Is he too polite to kick me out or does he really want to spend time with me? And all the while I just kept nodding and smiling. In the end, he didn’t ask for my number and I was too caught up in my own head to ask for his…I mean, I wasn’t sure if he’d be interested in having it!

At first after this encounter I was OK leaving it at that: a fun one night stand. Probably because I thought I could still eventually see this guy again through our mutual friend. A month has gone by and this mutual friend (the original friend with benefit) has moved on to another girl. I told him: cool, let’s hang out, introduce me to some friends! He declined (Ass…but I’m not really surprised there).
And now…I’m very anxious about whether I should add this other guy (B) over on Facebook. I mean, I WANT to do it. But also I’m afraid: Is it wise? Should I just let go? Maybe I’ll come across as pathetic? Creepy? Stalker-ish? What if he doesn’t accept the friend request? What if he DOES? What will our mutual friend think? Etc, etc, etc.

Needless to say, I’m clueless when it comes to guys. I still don’t know if the fact he didn’t ask for my number means he wasn’t into me or if I was giving mixed signals. I’ve discussed with my therapist that I might get in my own way when meeting guys by giving off an unavailable vibe. I mean, I could’ve been more enthusiastic when he mentioned plans. I know this unavailability comes from a fear of intimacy but I figured…well, the only way to get over that fear is putting myself out there (and having clear boundaries…also a work in progress) since I haven’t really come very far by understanding and analyzing why I might be afraid of intimacy. Also…I know, I’m insecure (but working on it!)

As further information, I’ve been single for a long, long time. I have been dating, I’ve tried apps, tried meeting new friends through meetups and other activities, and it hasn’t really worked out for me so far. I mean…maybe it’s another case of me getting in my own way, but usually I feel it’s a bit…inorganic? Especially dating has felt very forced. I know I prefer meeting people (guys) through friends, work, etc. That hasn’t happened for me very often, unfortunately. I know that this doesn’t mean it won’t happen but… I’m afraid I might have missed out on an opportunity with this guy. Maybe that’s why I’m so anxious about it?

I don’t know…should I just go for it? Add him? Take matters into my own hands? That’s what kills me, all this dating advice that says men should be the ones doing the chase (he did make the first move, though)…and I’m not sure I really agree! I don’t know what I’m expecting to come out of it, exactly. I mean, I’m trying to go about it with an open mind: I liked this guy and enjoyed his company, so I’d like to keep in touch with him, whether it’s as a friend or more (Ok, of course, I’m attracted to him and I’d like more but, seriously, someone different to hang out would be nice).

Any insight, words of encouragement or not, would be very much appreciated.