I [M28] keep meeting new people from time to time, at work, during bike rides, climbing gym, travels, and some few other places.

Some of the people I meet, we meet once, connect on social media, and I never see them again.

Others I keep meeting but in the same settings (bike rides for example)

Is there some tips and tricks on how to follow up with those people in order to see them more often, and outside of the same setup we’ve seen each other at ?

In other words, how do I ask people out to hangout ? (I also need to cross-post this in r/dating_advice cause I also don’t know how to ask women out on dates after meeting them once or twice)

Thank you 🙂

1 comment
  1. It’s tougher with people you’ve met only once. With people you see more than once, it’s important to remember their name, USE their name, and strike up a friendly conversation with them each time you see them. That’s how you get to exchange some casual information and strike up a rapport. After several conversations, once you feel like you’ve got a vibe going, THEN it is time to invite them to do something with you OUTSIDE the place where you know them from. Something simple like: grab a bite to eat, go for a walk or run, shop for something, hang out at your place, check out a new part of town, do an errand together, get something to drink, etc.

    You might have to to the inviting the first few times. After that they should also start reaching out to you. In between times you can check in with them using a BRIEF text.

    Also I’d do this with multiple people so you don’t have everything riding on one person saying yes.

    To make it even easier, instead of inviting them, you can make it more of a suggestion that they tag along with you. e.g. “Hey, I’m gonna grab a coffee at Java Joe’s after this. Wanna come?”

    That way there’s no pressure.

    That’s how I’d start.

    Good luck!

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