Thought I'd reply since guys keep asking why there are no women putting their 2 cents in...
I do not think "all is lost", in fact you may have actually upped your chances. Simply by seeing her a couple more times or getting more chances to make conversation. I think that the advice to constantly ask out random strangers because the higher number of women you ask will presumably give you a greater chance that one of them is going to say yes is foolish. Besides, I don't think you are interested in just
any woman, (nor are most men, contrary to what they might jokingly say), there is a reason you are obsessing over this particular one rather than any/every woman you see.
The main factor in whether I would say yes when someone asks me out is whether I have gotten to know him, at least a little bit & if he has "built the attraction" a bit by talking to me &/or flirting with me. If the woman can't tell you are at all interested because you are too shy to even talk to her, she probably won't have even thought of you in that way or about whether she'd like to date you. Women don't want you to act desperate or smothering, & it's true that some women do like the man to play a
little hard to get once they are already dating, but most women do not
get interested in a guy if he doesn't act like he is interested in her. Also, contrary to other advice given here, many women, myself included, are not going to say yes to a random stranger she just met asking her out, regardless of whether she thinks he is good-looking or has nice clothes, or he gave her flowers. This is simply because
he is a stranger. If the exact same man got to know her a little bit, had a conversation with her, even a short one, on more than one occassion, & acted somewhat interested, she would be far more likely to take up his offer of a date. Another reason a woman does not like being asked out by random strange men who she has never met before is that then she KNOWS that they are either only asking her out
solely because of her looks, or that they are one of those guys that asks out every woman they see, & they don't actually give a shit about her or whether she says yes. If you have flirted/talked with her a few times, on the other hand, then she may at least
think you are specifically interested in
her & like her personality etc.
So personally I don't think the giving a random stranger flowers idea works, maybe if it's just to brighten their day, but not if you are trying to get a date out of it. And I don't think that most women would think you are a loser or a creep even if they realized that you had made up a phony excuse to come back & see her or ask her out. I would think it was sweet. And, if you are actually doing it to try to get dates, I wouldn't bother asking out random women you just met or walking down the street, however it might be a good idea to do that simply just to get used to rejection. Then you might have some practice & not be as nervous when it comes to asking out a woman you are really interested in.
So in closing I certainly hope that you find the courage to just ask her out! You have nothing to lose. But even if you chicken out
again, IMO there is no harm in coming up with another excuse to go back & ask her out. You could even be honest & say "I came back here just to see you". That line has worked on me!
PS - as I said, I do not agree that you have hurt your chances in any way by not asking her out right away, in fact I think you have likely increased them. If you want advice on what to say or do when you see her that might help "tilt things in your favour", I would say try to talk to her as much as you can before asking, rather than just asking her out out of the blue, especially if you haven't done much talking previously.
Don't bring her flowers, especially not a huge expensive bouquet, a lot of women
do find that creepy, unless they are less attractive &/or older & rarely get any attention from men. Try not to act nervous or desperate, but don't act like you couldn't care less either. Don't use any cheesy or crass pick-up lines, semi-honesty is often best, like saying something like, "I have been enjoying seeing you every time I come here & couldn't help wondering if we could get to know each other a bit better," or, "I really didn't mind that I had to make another trip here, because that meant that I would get to see you again. Would you be interested in going out for a drink after work so that we can have another chance to talk?" etc. And if she says , "I'm busy after work" or makes some excuse, say, "That's ok, when do you have some free time this week?" If she
still makes an excuse & doesn't offer an alternative date or her number, then maybe it is her way of trying to politely decline. No harm done. Good luck!
