Whenever I can find them. Now that I think about it it's the finding of them that's largest sticking point.

I live in a small city and given my age (v late 40s), finding even remotely age-appropriate (c.32-42?) single women seems to be harder these days.
Younger than that frankly, I just don't find them to be mentally interesting. They might be fine for a quick shag I suppose, but I don't just want a quick shag with a flighty, frivolous, vacuous air-head... time is running out and I want a meaningful relationship. I sometimes approach young hotties just for the practice, but I don't have an agenda.

But meetups, parties, weddings, dinner parties.... sure, I'll approach anyone, no problem.

Back to dating sites, they strike me as a waste of both money and time - huge amounts time.
I'm probably just not photogenic enough, but either way I get a lot more traction with ladies in the real world.

J