Two and a half days ago, my friend Jill and I went out for dinner to celebrate her new job. While we were out, we both noticed that our waiter was "giving me the eye", if you will. He was really cute, and I'm 97% sure he was interested, but by the end of dinner, I completely chickened out and left without asking him out or giving him my number.

So now, along with about twenty other things that are going through my mind (work, home, work, cleaning the apartment, work, etc.), I can't stop thinking about this guy, whom I've never really talked to, whom I don't know at all, but who was obviously interested in me, which is something that I shouldn't really overlook, and who seemed really nice and was completely adorable, and who already has the approval of one of my friends....

I'm thinking about going back and asking him out. Saying something like, "look, I was here a few nights ago with my friend, and I never do this, and maybe I'm making a total ass of myself, but would you like to go out for dinner sometime?" So, my original question: Would that just be weird?

And, so this isn't just a thread about my (currently inept and non-existant) love life, anybody here met someone in a quirky, quasi-Hugh-Grant-romantic-comedy kind of way?

I reckon you should just go back as a customer and try and get served by him, and then strike up a conversation...

Less Hugh Grant, more Reese - I met Josh at the campus activities fair, which I was attending with the purpose of snaring a fellow freshman. I ended up sticking with the other guy for about two months before I cheated on him, then promptly felt huge quantities of remorse and broke it off just before finals. Somehow, my grades didn't suffer.

Back on the original topic, go for it. You can either go that approach, or then there's the patented Office Space approach - just stop caring about social mores entirely and ask him out mid-shift.

Me? Watch too many movies? Why, whatever gave you that idea?

Absolutely you should. That would qualify under the "meet cute" rule, thus qualifying you for romantic comedy-style bliss in no more than five reels.

There may be a series of quasi-comic misunderstandings before the bliss, though; these will possibly involve a cleans-up-nice (and formerly considered "plain") girl getting a drink thrown in her face and down the first fancy dress that she's ever owned, or injuries to one or more male crotches with hilarious overtones.
 

In Response to gtyrrell (#28814):

Don't forget the pet who has to steal some scenes and have one or two mishaps with the new man.

In Response to Rich (#28820):

Also, don't forget that Daubergoat is gay.

In Response to zamphir (#28821):

For the purposes of this discussion, sexual orientation is irrelevant. The rules of meet cute, the drink down the dress, and humorous crotch injuries are universal.
 

In Response to gtyrrell (#28824):

The rules of meet cute, the drink down the dress, and humorous crotch injuries are universal.

yes, but it's not nearly as likely to be a girl in the dress... at least, biologically... for now, that is...

In Response to zamphir (#28826):

I'll just state for the record that, no matter where we go from here, this isn't going to be pretty. Neither, for that matter, is the image of me in a dress.

In Response to daubergoat (#28830):

no matter where we go from here, this isn't going to be pretty

I'd thought Fire Island was supposed to be nice this time of year?