When is it okay to ask someone out?
June 13, 2010 8:56 AM Subscribe
Great with online dating, not so much in the real world. How can I better recognize when it's okay to ask someone out?
I know the question is incredibly broad, but this is something that I've been wondering about for a while. While I currently manage to maintain a reasonably active dating life, virtually every time I've met the girl in question online. These never go past 1-2 dates, usually due to a lack of physical chemistry (although a few have been due to other issues, the lack of in-person attraction is the most common).
I've been doing a lot of introspection and believe that the very nature of online dating may be my biggest enemy. Jumping straight into dating a perfect stranger just doesn't seem to do it for me. I believe it might be possible to find someone who is right for me this way, but I honestly don't find the "weeding out" process very fun or exciting - despite attempts to make the dates more fun, there's just too much pressure and too much to measure up against.
Those few successes that I have had dating-wise have been from meeting someone initially in an unrelated environment once or twice (maybe through a group activity or going out with mutual friends), talking with them a bit, we click, and somehow that leads to dating.
The thing is, I've only had that happen to me twice in the past few years: the first time, I asked her out purely for the hell of it figuring she would say no; the second time, the girl was the one who asked me out. Both times we clicked incredibly well and only called it off for reasons beyond our control.
So, my question is how can I increase the frequency of these sort of dates without looking creepy or desperate? By this, I guess I mean when is the appropriate time to ask out a girl I've only recently met, say through a mutual activity? I'm afraid that too soon makes me look like a creep, too late and she might lose interest. As of now, it feels like I have no idea when it's acceptable, short of having a girl flat out tell me "maybe we can get a drink/coffee/etc sometime" or something equally obvious. I can sometimes recognize things like flirting and other indirect cues, but am horrible at interpreting them - for example, I can't tell the difference between "I'm just having fun" flirting and "I'm doing this because I like you" flirting with intention.
Again, I know this is a rather broad question, but any suggestions/advice/etc are welcome...