Alright, here's a scenario for you. You meet a girl who you know you'll probably be seeing on a regular basis (at work, at the gym, in a store you go to a lot, whatever). You commit the cardinal mistake of not going for the number/making your intentions known right away. You keep seeing and talking to this person over a matter of weeks or months, but still don't go for the number. Eventually you decide it's time to be a man and go for it, BUT by this point it would seem awkward being as that you haven't done it by now. How would you (assuming you made this really dumb mistake) handle the situation.

I'm in this type of situation right now. Have known this girl casually for several months, see her once a week or so and have short conversations when I see her (about school, her job, small talk). I've gotten to a point where I know it's now or never, the time to grab my b@lls and go for it or else decide to forget this one for good.

Now,
Should I have asked for the number right away? Hell yes.
Did I f-up royally by not doing so? You better believe it.
Did I hurt my chances through hesitation? Uh huh.

Bottom line though, what's done is done. In your opinion:
1. Is it even worth giving this a shot being as that I've already waited so long?
2. If it's worth a shot (I figure I've got little to lose), what would be the best way to maximize my chances? After several months it seems like asking for the number out of the blue would seem odd.

Thanks for reading; I'm interested in hearing opinions.

I would say go for it, just like you said, what do you have to lose? It will only seem akward when you ask for the number if you make it akward. Go for it.

Thanks - I guess that's a good piece of advice for any situation.

It's simple...


Start up a convo, make her laugh with jokes. Then let a short lull in the convo creep in so you clear out some 'space' for your delivery. Then just say this.



"D'Arcy, I've known you for a while now, but it's the strangest thing: until now I haven't seen you as the type to date. How would you like to sit and REALLY talk over some coffee at the [The Coffee Bean on Sunset Blvd -- insert your preferred coffee shop here]?"



This approach is straight up, honest, not contrived or trying too hard to be slick. It's also a slight neg-hit since it implies that she isn't suitable dating material. This may work quite well if she is at least above average in looks. It will also work on insecure, rather unintelligent, superficial girls who think that they only thing they have going for them is their looks.



Try that on for size, and let me know how it goes.

It's simple...


Start up a convo, make her laugh with jokes. Then let a short lull in the convo creep in so you clear out some 'space' for your delivery. Then just say this.



" [D'Arcy], I've known you for a while now, but it's the strangest thing: until now I haven't seen you as the type to date. How would you like to sit and REALLY talk over some coffee at the [The Coffee Bean on Sunset Blvd -- insert your preferred coffee shop here]?"



This approach is straight up, honest, not contrived or trying too hard to be slick. It's also a slight neg-hit since it implies that she isn't suitable dating material. This may work quite well if she is at least above average in looks. It will also work on insecure, rather unintelligent, superficial girls who think that they only thing they have going for them is their looks.



Try that on for size, and let me know how it goes.