When and how to approach girls in Meetup groups

[Dannyboy]

So, I've gone to a couple of Hikes for this 20s and 30s hiking  Meetup and met a couple of really cute girls. I'd love to ask them out but I've never asked a girl out physically ( I've only asked out girls on OLD before) and I'm not sure what's appropriate. I have talked to these girls before on a friendly basis, but I've never tried flirting with them to gauge if they would be interested because I don't want to creep them out and because I rarely have a chance to speak one-on-one with either of them. I'm not even sure if it's alright to flirt with and ask out girls in Meetup groups. In addition, I'm just not sure how I compare attractiveness-wise to the other guys in the meetup group. What should I do? Should I wait until I get to know them better? Should I avoid asking anyone out unless they've shown clear sign of interest?

[Enail]

I think in a situation like that, you've got to be a little careful that you're treating the meetup like your personal dating pool or coming across like you're just there to hit on every pretty girl you see. I'd suggest slowing your roll a little, get to know the girls you think are cute, and only get more flirty/ask someone out if you find you like that person specifically once you know them a little better. Not that you should try to be totally platonic bffs or anything before you can start flirting at all, but just to have enough interactions that you have a sense of who they are rather than just what they look like, and to have a sense of if you even enjoy interacting with each other.

And also get to know people other than cute girls, that way you can meet potential friends and have more general connections in the hiking group, and it also means you're less likely to come across like you're just there to trawl for dates.

[Werel]

Agreed with everything Enail said-- wait long enough to see if you click with one of them as a person, and then see how they respond to flirtatiousness or a date invite. You don't need to wait until they've shown clear signs of interest (asking someone out is gauging their interest, after all), but you should wait until you're sure you're actually interested in them.

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