I’m in upper 30s, dating after a LTR. Long enough that the online thing and apps thing is new (I’m no Luddite though—I’m talking apps specifically in a dating context). I’m returning to this and have just started going on two or so dates a week. I’m just trying to loosen up again and walk through the world with ease. A lot of the general dating advice out there—newspaper, women’s mags, etc seems terrible and cliche, something off about it (it’s like the movies! Too perfect) so thought I’d seek out your views on my situation and if age matters.

I go to bars often with a close group of 4-6 mixed friends, work 9-5, live in a big city in a central location, and some weeknights are often dedicated to “hobby/self development/interests”.

A couple things I’m curious about:

  1. I have a very low tolerance for flaking—not just in dating—so I’m really only talking to 28/27+ working professionals. Is general dynamic with 24yo and 34yo different or “women are women”?

  2. My personality is chill more reserved. I’m not hi-fiving half the bar, “bringing the party”, or the comedian of the group. I worry that I may be too much of a “nice guy” vibe because of that.

  3. A lot of advice here is to go all the way right away when dating, and that second dates should always be at your house. I’m finding 1st dates straightforward to setup but this “Activity 2nd date vs Meet at your home” is tripping me up for 2nd dates. On which side is it better to err for older women?

  4. For 30s +, how often are you dating and which apps do you find worth it?

  5. My friends say my strong qualities are: good at connecting friends, social organizing, good listener, non-judgemental, curiosity.

  6. I’m not “hunting” and trying to notch up a count, but also I’m not looking for a life partner. Somewhere in the middle, I don’t know if that’s trying to have it both ways. I’m not opposed to a relationship, but wouldn’t want something so serious right away.