Instead of busting on this guy anymore, I'd like to be constructive and try to help him (in case he's reading) and anyone else who finds themselves in a similar situation.
First, it goes without saying you should never "ask out" a woman where you hang out. Or where you work. Because if she says no -- well, look at what happened.
So what do you do? Simple: flirt in the margins. Make smart comments. Involve her in your group. Get her group to meet up with your group. Socialize as if it's high school (life really is high school in a way). Keep it light and flirtatious.
I know some of you might think "Wait -- but he'd get friend-zoned that way." That would not necessarily happen. You can't be friend-zoned if you're not friends per se. If he sticks around making Roissy-type comments and observations, he'd be too aloof to friend-zone.
So how could he have eventually moved in on her and made it work?
Easy: the way I did. I made this work by turning the tables. If you build flirtatious rapport with a woman yet don't ask her out, she starts to unconsciously think you've rejected her and/or something is wrong with her.
This was my way of operating in my old office (which I'd mentioned in previous posts). I knew I couldn't ask women out directly because rejection would make coming back to work too awkward. So I'd hang out with them, flirt with them, but never quite "move in" on them.
Eventually, I drove at least three of women (on different occasions) to the point where they were exasperated with me. Two of them asked me out directly and another asked me what the eff was up with me and was I gay (hahahaha). But this changed the dynamic and let me avoid the sorry situation this guy ended up in.
This guy could have done all this. Or he could have used some of the other techniques I've mentioned on here: asking to borrow money, asking for a ride home, etc.
I really think the concept of directly asking out a woman is dated and guys need to find ways of doing it without doing it. These are not women from a 1980s sitcom you're dealing with. These are jaded women who have grown up with social media surrounded by lapdog Betas. Uncle Jesse and Aunt Becky's romance is the stuff of days gone by. You try to make like them and you turn yourself into Urkel.
First, it goes without saying you should never "ask out" a woman where you hang out. Or where you work. Because if she says no -- well, look at what happened.
So what do you do? Simple: flirt in the margins. Make smart comments. Involve her in your group. Get her group to meet up with your group. Socialize as if it's high school (life really is high school in a way). Keep it light and flirtatious.
I know some of you might think "Wait -- but he'd get friend-zoned that way." That would not necessarily happen. You can't be friend-zoned if you're not friends per se. If he sticks around making Roissy-type comments and observations, he'd be too aloof to friend-zone.
So how could he have eventually moved in on her and made it work?
Easy: the way I did. I made this work by turning the tables. If you build flirtatious rapport with a woman yet don't ask her out, she starts to unconsciously think you've rejected her and/or something is wrong with her.
This was my way of operating in my old office (which I'd mentioned in previous posts). I knew I couldn't ask women out directly because rejection would make coming back to work too awkward. So I'd hang out with them, flirt with them, but never quite "move in" on them.
Eventually, I drove at least three of women (on different occasions) to the point where they were exasperated with me. Two of them asked me out directly and another asked me what the eff was up with me and was I gay (hahahaha). But this changed the dynamic and let me avoid the sorry situation this guy ended up in.
This guy could have done all this. Or he could have used some of the other techniques I've mentioned on here: asking to borrow money, asking for a ride home, etc.
I really think the concept of directly asking out a woman is dated and guys need to find ways of doing it without doing it. These are not women from a 1980s sitcom you're dealing with. These are jaded women who have grown up with social media surrounded by lapdog Betas. Uncle Jesse and Aunt Becky's romance is the stuff of days gone by. You try to make like them and you turn yourself into Urkel.