My wife and I live above a bar frequented by tourists and the bartender is a friend of mine. When it isn’t busy, I’ll usually go down there order a soda and just talk to whoever shows up. The easy opener once the conversation starts is “what keeps you busy?” and keep the conversation going. This lets them talk about work, family, hobbies or whatever else they like to talk about

I read a book that said you should try something new to you at least every quarter if not more often. It gives you something to talk about.

While my wife and I are empty nesters and at point where we travel a lot and we do the digital nomad thing in spurts so we can always talk about travel or more often ask “what’s the most interesting place you’ve been to”/“What’s interesting about where you live” etc, it doesn’t have to be travel.

And just to be clear, it’s always either guys I am striking a conversation with or couples. There is no way for a 50 year old married guy to talk to a woman alone at the bar without coming off like a creep.

On the other hand, I try not to talk about politics or religion. What’s the point?

> I read a book that said you should try something new to you at least every quarter if not more often. It gives you something to talk about.

Any chance you remember the name?

> There is no way for a 50 year old married guy to talk to a woman alone at the bar without coming off like a creep.

Not true. You have to engage in a way that signals very clearly you don't really give much of a shit about talking to her, and your social status is higher than hers.

For example, if you're having a conversation with your bartender friend and you need a female perspective to settle a disagreement, and you ask for it without fully "engaging" with her, that'll work fine. Once she's been pulled in you will have to keep hooking her into the conversation with interesting tidbits, but eventually most women will just keep talking.