Okay, I'm going to try and give you the cliff notes version of this, as it's kind of a long story. So two of my best friends, who were dating, are not dating anymore. She is trying the "friends after dating" thing, and he's still a bit bitter over the break up, something I see that she does not. Because there are two friends, I have two situations.

Situation 1:

The female friend has been experimenting with her sexuality for a while, trying to figure out if she's bi, lesbian, straight, whatever. We got to be really, really close toward the end of their relationship, and it wasn't until (semi) recently that she admitted she had feelings for me, extending beyond mere friendship. Feelings that I didn't exactly reciprocate. I should mention that I've both made out with and slept with this particular friend (both somewhat inebriated), which was perhaps my error. But at the time I told her exactly how I felt. Things have died down for the moment in that regard, but I feel like it hasn't gone away...the subject is merely hibernating.

Situation 2:

After the break-up, I started hanging out with her ex-boyfriend a lot, partly because I felt bad for him...he doesn't have a lot of friends, and I knew he'd taken it pretty hard, even if he didn't show it. But the more time I spent with him, the more nervous I got about remaining just friends with him, considering he's single again. About a week after the break-up, I got an email from a mutual friend, asking when we were going to "make it official." A conversation that turned into, "so you've never thought about it?" Which I told him I hadn't. Her ex had always been big into "the game," "the chase," or whatever you want to call it...something I've always been somewhat oblivious to, and I can't help the feeling that he's "pursuing" me.

He always finds excuses for me to end up back at his apartment to hang out together, hits on me constantly (although that hasn't changed...he tends to be the flirty, full-of-shit type anyway, but it feels different, as if it's not all in jest, now), and he'll say things when I mention hanging out with people, something along the lines of "well why don't you want to hang out with JUST me?" He hasn't come out and said anything about dating/a relationship/whatever, but I know this friend, and I know I'm not imagining it. He's a great friend, but jumping into a relationship with him would fuck a lot of things up, plus I know it just wouldn't work (for one, he's 33, I'm 21). I'm not very good at 1. confrontation or 2. back-peddaling in a friendship when I've gotten in too deep.

Situation 1 doesn't know about situation 2, and situation 2 doesn't know about situation 1. Help?

I'd like to remain friends with both of them, but am I making a mistake spending so much time with friend 2? I really like hanging out with him, and I try to be careful not to send out any "signals" he can misinterpret, and he's been a REALLY good friend to me, I feel almost like I owe it to him. Which we all know is a really terrible reason to go into a relationship. Any thoughts?

Edits 1 & 2: Spelling and grammar

Edit 3: Adding edit messages.

You definitely don't owe it to him to lead him on, especially by accident. What do you want out of this?

I think you need to make your wishes clear to the guy. If people are already asking when it'll be official then you aren't being friendy.

Posted by AnAppleSnail I think you need to make your wishes clear to the guy. If people are already asking when it'll be official then you aren't being friendy.

Well I think in the beginning he was teasing me, he tends to do that. Plus, I still haven't figured out if he was put up to sending me that message (but I have my money on yes).

Any suggestions on how to "make my wishes clear"? Nothing's been mentioned in that regard, and I don't know how to do it without having the awkward, "Sooooo, I really don't like you that way" conversation, although that might have to happen.

You weren't necessarily leading him on, some guys are just pompous and will flirt with the whole world and assume when women aren't bitches in reciprocation it means they like them.

Friend 1 will get over you, especially if she isn't sure what she is or what exactly she wants yet. Or, she won't and you can deal with it later. Sexual relations with friends is never something that seems to end well unless you have really clear boundaries on the whole thing - which is impossible while inebriated.
Hopefully she'll narrow down her wants and needs, and if you still fall in that category then there will be another conversation down the road - who knows, you make think she's the bees knees later on and she might be onto her next flavor of the week already.

Friend 2 needs to be spoken with directly, just once, to be made clear that you are in no way pursuing a relationship now that he's 'on the market'
If it were my conversation, I would mention a friend had asked about the two of being together and lead into telling him you in no way want to portray that to other people although he is a great friend, and that you should spend time with other people more often.

I hope I helped, if not maybe somebody has better advice

What girl hasn't made out with her friends drunk? And by slept with I assume you mean actual sleeping... in which case what girl hasn't?

When people come out it's somewhat common for them to crush on their best friend and hope that said friend is in the closet. It's one of those patterns that turns up all over the place (according to dan savage, my reference for all things gay). It'll probably hibernate for years, or at least until one of you enters a serious LTR. A little awkward, but nothing you can't laugh off.

As for boys: It's always more than joking. I mean, yeah, it's a joke, but if you whip off your shirt and say "Nah, but seriously lets have sex" they aren't gonna be like "No, no, it was in jest".

But saying things like "but why don't you hang out with just me" is desperate / creepy / indicative of dependency?

I think you could solve all your problems with a different boyfriend! It doesn't even have to be a real boyfriend. Just go on a few dates with some boy (boys for dates are easy to find. Bars, Facebook, okcupid, uer.ca/love .... you know, all the big names in dating), then tell girl A you are dating a boy and he has a great cock, and tell boy b that you can't hang out as much because you need to spend time with the boy, or tell him he can't say (the creepy) things because you know it'd hurt the new boy's feelings, or whatever. A little non-confrontational, but it should work a treat.

If it doesn't, you might have to avoid spending time with him. I just had to do that to a girl because no matter what I said ("we are just friends, and will only be friends") she thought we were in a relationship ("I love you"). I told her that I have to be honest in my relationships and felt that I was misleading her with my actions, so I needed some distance... and it seems to have worked. Surprisingly little drama-bombing.


And for "owing him" being in a long term relationship.... you'll grow to hate him for it if you do it. As an aside, is he emotionally manipulative? Some people are because they are dicks, and some people are without even realizing that that is what they are doing.

I disagree with MindHacker. There's no need to be deceptive. I agree with Yield, for the most part, though I'm going to say that you screwed up by making out and having sex with your female friend. I certainly hope that didn't happen while she was still in a relationship with the male friend. That makes it much worse.

Edit: Just a punctuation correction.

You guys have all been great, thanks.

I kinda figured the thing with friend 1 would pan itself out. And no, Mindhacker, I mean "slept with" as in had sex with, which WAS my bad. At the time I went into it purely for the physical aspect, and I assumed she did too. And no, that was not while she was still in a relationship, even though they were technically in an "open" relationship toward the end (although both of them admitted to me on different occasions that they wouldn't be able to go through with sleeping with someone else).

I'm really, really terrible at confrontation, so I kind of like Mindhacker's option, even if it is slightly deceptive. The other part of me wants to wait until he says something about it, and then set him straight. The last thing I need is friend 1 thinking that I'm "stealing her boyfriend," or somesuch, especially considering I know she still has feelings for him. The wierd thing is that she's asked him about it before, after the break up, saying things like, "Are you sweet on _______?" and he's, apparently, (he told me later), responded with "Of course not." But I'm just getting to many bad vibes in that direction.

Anyway, thanks so much for all the help. Mindhacker, I didn't know that it was common for gays to crush on their best friend when they came out, and that reassures me a lot. She'll get over me, and hopefully we can remain friends.

I think you've gotten some pretty good advice thus far. I'll just add that once upon a time I dated a guy because I felt like I "owed" it to him, and it ended up being the worse, most abusive relationship I ever had. Don't do it.

I defer to the Rabbit's expertise on this matter.