I know people who really get into exactly the time they should show up.
Like, they like to show up exactly 11 minutes late, so they don’t look too eager, but they don’t look rude or like they tried to show up late. There are all these weird rules in place and you can get into your own head. Either your date will like you or they won’t, and if they don’t, who fucking cares?
I think a lot of guys when left to their own devices default to those kinds of generic dates because it’s simple and it’s not off-putting.
Suggest a hobby you’re into, like hiking or something.
If the conversation flows that way naturally and you’re both comfortable sharing that kind of information, then go ahead and roll with it.
For example instead of asking about places she’d like to travel you can start by stating the places you would like to go to.
After you open up she’ll feel more comfortable doing the same.
It was a really great ice breaker while we grabbed drinks at the bar, and it’s an easy game to play and screw around with.
I mean, obviously, you can’t really play with two people, but it was fun to have something stupid to laugh over.” —“Try and go somewhere other than dinner and a movie or drinks at a bar.