Almost feel bad for asking women out...?

[robertdawson]

So I've sort developed this problem....

There have been so many times where I mistook conversation from a woman or friendliness as being interested or flirting that I've become incredibly risk averse. It is almost like I assume they're just being friendly because I feel like an idiot or an asshole for asking them out and making them uncomfortable when they were just being friendly. This effect is intensified with someone I know because I don't want to lose whatever sort of relationship we already have (burning bridges basically).

Just yesterday, I was at a bar playing pool and there was a group of girls sitting off to the side of the table. I noticed that one of them was a girl I worked with for a little while about a year ago so I walked up to her and was like "hey you worked at such and such right?" After talking to her for a few seconds her friend (who was sitting closest to me, the other girl was.a bar stool back) turned around on the stool and smiled at me. I kept talking to the other girl and to be honest, I can't remember now, but I'm pretty sure she did this again a few minutes later.

I was going to say "so who's your friend here?", or more boldly "so who's your pretty friend here? which I would think could potentially make both of them uncomfortable and make me look like an idiot. Anyway the reason I did not was I was thinking "dude, she is just smiling at you because you're talking to her friend, don't be an asshole and make something out of it it is not". So after I was done talking to her I just kept playing pool. Later on her friend was leaving and as she was walking past me she smiled at me again and I smiled or did some sort of acknowledgement. Anyway, obviously she left and nothing came of it.

Thinking back on it should I have said either of those things at the start? Would the first one have made it clear enough I was interested or would I have had to try to riskier flirty one? If I hadn't said either of those things should I have stopped her as she was walking past on the way and out and said something like "hey, I never caught your name. Blah blah. I'm going to lunch at such and such tomorrow, want to come?"? On one hand it is a calculated risk but on tbe other hand I feel like a doofus for asking a girl for her number and to lunch after JUST meeting her; it feels stupid.

More generally, how do I deal with my problem? Should I just take the risks anyway? I feel like if I took a shot every time I thought a woman *may* be interested I'd be one of those guys that comes off as desperate and honestly I'd feel like a doofus for asking so often. I guess part of that is because in middle and high school if you went around asking a bunch of different girls out word quickly spread that you were desperate and ridicule was sure to follow. Obviously college is a much bigger place but the same idea applies.

[Kroda31]

Right there with you.

Interested in what people have to say about this.

[bloodtippedrose]

Well obviously nothing is going to come out of you not saying anything. If I was the girl giving you smiles I would have at least liked to have been introduced to you, even if I wasnt interested in a date. If you said the "pretty friend?" It would have been embarrassing to smiley and a little rude to the girl you used to work with. Asking to be introduced in the "whos your friend?" or "Is this a friend of yours?" would have been appropriate because its not really a come-on, its just being nice and was a missed opportunity to learn more about her.

It also would have been good to stop her and say you didnt catch her name and see what she had to say, but not ask her out to lunch right away unless she seemed really interested which probably wouldnt have been the case. To ask her right after asking her name on a date or for her number is sort of a put-off, especially if you had a chance to talk to her all night and didnt.

As far as your problem in general, there is no black and white answer to it, you have to make judgement calls and risks, and know when to just let some go. But, as i said before, not saying anything will get you nowhere (except give you regrets). If a chick is making repeated eye contact and smiles at you, id say shes worth the risk. If you see a cute girl who laughs at one of your jokes then takes a hike to chat up other guys, shes probably not worth the risk. You know the signs of flirting, so if you see them don't talk or trick yourself out of acting on them. Also you don't have to put yourself out there and ask for their number everytime, just introduce yourself and be nice and genuinely interested in the conversation.

[KingZ]

A woman much wiser than me once told me this:

"If it's something you could say to your grandma, then it's friendly. Else, it's flirty."

That said, it's not bad for you to initiate the flirting, as long as you're tactful. I would personally never say, "Who's your pretty friend here?" That's a turn-off.

[robertdawson]

Well, I guess I don't know how to flirt. The "who's your pretty friend" introduction is obviously awful (I pretty much knew this anyway), but I can't think of any way to flirt with a girl without it being potentially embarrassing or uncomfortable. I guess what I usually end up doing is asking them questions about themselves and talking with them more than I would any random girl I wasn't attracted to. Going back to the bar example: if I end up playing partners with a girl I'll give her high fives and such after her turns, but again, even though that is physical contact they probably don't think of it as anything more than friendly. The problem is is that most girls probably assume this behavior [talking, things like high fives] is being friendly because it is a very tame way of "flirting". I wish girls realized that if a guy goes out of his way to talk to her [or at least me] then he is interested in her/flirting with her. Really, think about my example, why would I bother asking her to introduce her friend if I wasn't interested in her?

If I had asked the girl who her friend was, what would I have done from that point on? I don't know how you would change that conversation from friendly "this is my friend blah" into getting a phone number. Let's face it, if you meet a girl in a bar you probably aren't ever going to see her again if you don't go on a date with her [barring miracles or crazy coincidences], so if you want a number you better get it while you are there. Last weekend a girl was flirting with me and I just assumed she was being friendly and didn't want to "risk it" and never got her number. Now I will probably never see her again. It is a terribly depressing feeling to have because women that are attractive as her only show me any attention every once in a blue moon.