Um… well, first off, flirting doesn’t have to happen when you’re hanging out. It can start with something as simple as a compliment to a stranger. Start from the premise that people like to hear positive messages about themselves without any strings attached, and hand them out like candy (but recognizing that taking candy from strangers is something some people would prefer not to do for obvious reasons, so accept whatever response you get to what is offered) - some people will respond back, others won’t, but no harm will be done. I am an introvert so I don’t do this often, but striking up conversations with new people at random is a thing I can force myself to do, and it rarely goes as poorly as one might fear.
But also, my friend-group is mixed, more women than men, and typically it’s people I’ve met one at a time over the years, less of a “friend group” than “a number of people who are my friends”- so I have lots of 1:1 time with female friends. In terms of flirting with those friends, well, they’re friends, so that almost never happens—but almost never is not never. Three times that I can recall off the top of my head, it turned out that one of my friends was attracted to me, and I learned that either because she explicitly said so (in one case, we were teenagers and both clueless about how to flirt, her idea was to follow me around everywhere, and from my perspective I just didn’t know that was a thing that I should notice) or because of some flirting (two cases). When I was younger and much, much more awkward, there were innumerable instances where I was attracted to a female friend and didn’t say anything because from young-me’s perspective of course not that’s insane and I’m lucky this amazing person even wants to be my friend and allow me to continue to be in her presence. There was once when I did say something to a good friend and it wasn’t reciprocated, we’re still close friends, but that wasn’t flirting so much as “we’ve just met had lunch because you suggested it, and I’m feeling some attraction—you? Nope? Ok then, I still think you’re awesome and we should be friends”. There have also been a couple instances where I’ve met someone at an activity or through other friends or at work, hinted at an attraction, she’d hinted back, we’d done something low-stakes like going for a walk together or having a coffee, but it wasn’t an official date or anything, and there was some attempted flirting with mixed success in that context.
What I’m picturing if I was back on the dating market (I’m with a good partner currently, hopefully in perpetuity) is, if I met a woman outside of a dating app who I’d like to date or add to my list of woman friends, depending on how she feels (I tend not to date people just for the hotness, they’ve got to be someone I could be friends with too), we’d probably do something low-stakes 1:1 that wasn’t officially a date or not a date, and depending on how that went, either become friends, go on dates, or part ways. And in the initial figuring out how things were going to go, there would likely be some flirting. At least, I expect that’s how it’d go.
Um… well, first off, flirting doesn’t have to happen when you’re hanging out. It can start with something as simple as a compliment to a stranger. Start from the premise that people like to hear positive messages about themselves without any strings attached, and hand them out like candy (but recognizing that taking candy from strangers is something some people would prefer not to do for obvious reasons, so accept whatever response you get to what is offered) - some people will respond back, others won’t, but no harm will be done. I am an introvert so I don’t do this often, but striking up conversations with new people at random is a thing I can force myself to do, and it rarely goes as poorly as one might fear.
But also, my friend-group is mixed, more women than men, and typically it’s people I’ve met one at a time over the years, less of a “friend group” than “a number of people who are my friends”- so I have lots of 1:1 time with female friends. In terms of flirting with those friends, well, they’re friends, so that almost never happens—but almost never is not never. Three times that I can recall off the top of my head, it turned out that one of my friends was attracted to me, and I learned that either because she explicitly said so (in one case, we were teenagers and both clueless about how to flirt, her idea was to follow me around everywhere, and from my perspective I just didn’t know that was a thing that I should notice) or because of some flirting (two cases). When I was younger and much, much more awkward, there were innumerable instances where I was attracted to a female friend and didn’t say anything because from young-me’s perspective of course not that’s insane and I’m lucky this amazing person even wants to be my friend and allow me to continue to be in her presence. There was once when I did say something to a good friend and it wasn’t reciprocated, we’re still close friends, but that wasn’t flirting so much as “we’ve just
methad lunch because you suggested it, and I’m feeling some attraction—you? Nope? Ok then, I still think you’re awesome and we should be friends”. There have also been a couple instances where I’ve met someone at an activity or through other friends or at work, hinted at an attraction, she’d hinted back, we’d done something low-stakes like going for a walk together or having a coffee, but it wasn’t an official date or anything, and there was some attempted flirting with mixed success in that context.What I’m picturing if I was back on the dating market (I’m with a good partner currently, hopefully in perpetuity) is, if I met a woman outside of a dating app who I’d like to date or add to my list of woman friends, depending on how she feels (I tend not to date people just for the hotness, they’ve got to be someone I could be friends with too), we’d probably do something low-stakes 1:1 that wasn’t officially a date or not a date, and depending on how that went, either become friends, go on dates, or part ways. And in the initial figuring out how things were going to go, there would likely be some flirting. At least, I expect that’s how it’d go.