Is He Serious About This? (long)

[VampirePrincess]

I have a good friend, let's call him Dave. Dave and I have known each other for about 5 years, and we've been friends for 4 years. At times we've been like best friends, and right now we're definitely best friends. I've always felt honored because although he's not in the "popular" group, everyone likes him and talks to him, and I was surprised out of the huge group to choose from I'm one of the few people he chooses to see outside of a school setting.

Dave was never someone you would want to talk about relationships with. He was a complete innocent, never showing any sign of wanting to be in a relationship. And to top it off, if someone tried to talk to him about one he would stick his fingers in his ears and sing loudly. He's grown past that stage but he still looks rather uncomfortable if he has to listen to conversations about love.

About a month ago I was talking to Dave online and I noticed he was typing differently than normal. Many more smiley faces, and actually forming more complete sentences - or at least attempting to. His English isn't as good as it could be, at least for writing. He started correcting words that I spelled wrong and ending things with ... which I would normally consider flirting.

About two weeks ago my boyfriend quit talking to me and Dave was the first person I told about it. He was being all encouraging about how it wasn't a breakup silence, but he was still all smiles about the whole thing. He took a huge interest in the situation, talking to me every day asking me if I had heard from my boyfriend yet. It struck me as odd. Dave is a fan of gossip, but not about that topic.

A few days ago I found out it was indeed breakup silence and since Dave seemed so interested in what was going on I told him. He got upset because I was crying, and I guess he thought spilling his problems to me would make me feel better. He went on and on about how he hates seeing all these happy couples everywhere because he's never been in a relationship and he feels lonely, and that sometimes people trash relationships so much he never wants to be in one but most of the time they seem great, and he really wants at least one relationship in his life.

Last night he called me again and after a few minutes he brings up my old relationship, asking me how I was dealing with it. I told him fine, it was probably for the better anyway. Then he says that his parents want him to ask me out, so I asked him what he said. He said, "I said yeah because you know we've known each other for so long and everything but I don't know what to do!" so I asked him if he wanted to ask me out, and he said "Yes, or no, or I don't know but yes." Then he started telling me why his parents want him to date me, which ended up being a whole list of my good qualities so of course I didn't interrupt him during that. Then he asked me what he should do. I feel weird giving him advice on if he should ask me out. I'm surprised he doesn't feel weird asking me for advice on that. I told him relationships were complicated and before he gets in one he should think long and hard about if he's really ready for one, because there's more involved than what you see on TV. After a while he switched topics but then he came back with "so what are your turn ons...er I mean what did you like best about Kyle?" (Kyle being my last boyfriend) and then he moved down the list, asking me about a few other guys and then what I liked the least about all of them. Then he said he would like to ask Robert (a mutual friend who I've dated and seems to be fairly good at relationships) what to do, but he can't because Robert already thinks we're dating and to mess with him we both told him we were. And then he had to go, so I got left alone with my thoughts.

I would be lying if I said I didn't have any feelings for him. But I'm not going to date him if he's asking me out for the wrong reasons. If he really likes me, then yes, I want to date him. If he only wants to date me because his parents forced him to ask me, or he just wants to not be alone anymore, that's not good enough and I won't date him. So what does it sound like to you? I really can't tell...

[PlayingPretend]

Honestly, I'd be concerned for the same reasons, but no one here can tell you what's going through his head. He could really have feelings for you and simply used his parents' "want" as an excuse to be open about his thoughts and feelings, or it could really have to do with the fact they want him to and/or he's lonely. I'd sit him down, and tell him that whether or not you'd advise him to ask you out really does depend on whether or not he has honest feelings for you. That being said, it's not been very long since you broke up with your boyfriend, from my understanding, so I'd be careful you don't end up in a rebound relationship. In your shoes, I'd probably tell him that I wasn't yet ready for a relationship. I'd take the time to heal from my break-up and then consider dating again.

[StabMyHeartLover]

I don't think its casue of his parents, that sounds more like becaseu of an acncuse he's made up. But if you think that is why , just ask him. Thiers no need to rush things, so try letting him know that

[PSY]

Awkward, much? =P You won't know for certain until you sit down with him (in person would probably be best) and try to get into his head. Is it doing this simply because he's lonely? Or does he genuinely like you? That's something you can't really figure out, based on how someone acts over instant messenger. You have to spend time with them, get to know them better (and vice versa), see how they are in a "dating" situation, and most importantly, don't rush into making a decision. If it's just a crush, then chances are he'll back off after a few weeks, when you don't immediately say "yes". If he's just lonely, then he may start hitting on someone who isn't "hard to get". If he really wants to be with YOU, however (and it's for the right reasons), then I think you'll be able to determine that after a few weeks. =) Good luck!

[WillO'Wisp]

It does sound like he genuinely likes you, but he doesn't sound too sure and neither do you.
I think you should ask him if he's asking you out because his parents asked him to, or because he really likes you. Just tell him you want the honest truth.

[rednailpolish92]

from my perspective, i think he might be trying to push HIS feelings onto those of his parents because hes afraid that you dont feel the same way. i think that he feels that if he blames it on his parents and you reject him (cuz if he feels lonely and has never been in a relationship, he might not have the confidence you do) then he doesnt feel like its because you dont like him. see what i mean? i think hes trying to protect himself. id say go for it... not too serious at first, but obviously he is interested in you.

[VampirePrincess]

Thanks for all the replies, everyone. That's mostly what I thought too - that it does sound as if he likes me, but he might not and I'll have to wait until I talk to him in person to find out.

The sad thing is, I'm already fairly sure he wouldn't be good in a dating situation. If we're at the mall or something and I end up holding onto him to make sure we don't get separated in the crowd he tenses up and half turns away from me, I can tell it makes him uncomfortable. I have a friend who holds my hand in public sometimes and Dave commented on it the other day, saying that "things like that should only be done in private." Holding hands, really? Come on. Maybe it's a cultural issue or something.

I do plan on waiting for my next relationship, I used to do rebounds all the time and I can't stand them. I'm just not sure how to act around Dave until I know how serious he is about wanting to ask me out, because I don't want to feel like I'm leading him on. I would go out with him, but...not for probably another month at least.