Mixed Drinks, Mixed Signals: I like my newly single bartender

I met him exactly two months ago. Let's call him Tom. My boyfriend of a year had recently broken up with me, so I've heavily considered whether or not this is a rebound crush, and it's definitely not.

Two months ago, a day before Christmas Eve, I walk into this bar with my friend Anna, and I meet eyes with Tom. Spark. He pays for our drinks. The bar is packed, but he keeps coming back to us to make small talk...I'm drunk and starry-eyed.

Flash forward two weeks. We go back, he remembers us and buys our drinks again. Anna tells him that I'm into him; he replies, "It's definitely mutual...but I have a girlfriend. I'm trying to get out of that relationship, though."

Let's flash forward another couple of weeks. He's broken up with his girlfriend--of FIVE years--he tells my wing-lady Anna that he'd like to take "baby steps" with me (???)

I'm not pushing it here. I gave him my number a long while ago; I told him that I'd like to be friends; he said the same. I asked him out for a "baby steps" cup of coffee about one week ago, and we met...It was fun; we had a lot to talk about, a lot of shared interests. He's quite nervous around me, but he is definitely attracted to me, as I am to him.

I really, really like this guy, but I don't know how to act gracefully in this particular situation. Let's review the factors:

1) He just broke up with his girlfriend of five years.
2) He is very, very shy and somewhat intimidated by me (always telling me how confident I am [I am a bit of a guy magnet at the bar...but he's the only one that I want])
3) He always buys my drinks, always tries to talk to me at the bar, although it is very hectic.
3) He likes me. I swear, he does!!

We've been out once. He has my number, though he's never used it. He knows that I like him, and that I respect his space. What can I do? I'm not nuts; I don't want to jump into a relationship with him. I just want to get to know him on a platonic level, but I don't know if I should be the one to ask him out again, and I don't want to be all up in his business, especially after his momentous breakup. I may very well go nuts trying to figure this out...

Any advice is appreciated!!!

i think that you are doing the right thing by taking things slow. however, you are over reacting because you too have just gotten out of a relationship.

i'd say relax and give it a try.

raverboy

I have some advice. Be careful dating a guy that buys other girls drinks while he's still in a relationship. Remember: if he'll do it FOR you, he'll do it TO you.

I gotta say, i really like how your handling the whole situation. I agree with Ill and Giga too.

One time i went on a date with a girl and we had "relations", the next day, she tells me she has a boyfriend, breaks up with him. Later, cheats on me. Go figure.

I think your doing a great job, just relax, keep doing what your doing. He'll come around. Speaking as a shy guy ABOUT a shy guy: it takes us a little longer to do stuff =) But i'm sure it'll be worth it.

Thanks for the tips, all.

I've gone ahead and texted him for "baby step number two", but I'll have to wait this one out, since it's Mardi Gras tonight!

Head first, head first...I'm sick of letting the ones that I really like get away and settling for the ones who pursue me.

Good for you! Go with what/who YOU like...