How concerned should I be that his strip club-going past will be a thing for him to do again?

I'd suggest trying to figure out how big of an issue it is for you first. Is there a difference in your head between making that a regular part of your Saturday night, and him going like, once, because it was a bachelor party and that's where everybody wanted to go, and he didn't care to find somewhere else to go by himself for a few hours?

Is this just something you'd prefer he didn't do, ever, at all, and is a deal-breaker, or is it one of those "I really don't want to date a guy who is still hitting up strip clubs with his buddies on the regular at 40?"

Then, communicate your preferences and boundaries like an adult, whether that's dating a guy who does that on the regular, or whether you consider setting foot in one, ever, at all, to be an act if infidelity.

Also, remember that he has every right to accept or reject living under those terms, and your option there is pretty much to choose to accept that or move on.

I assume that at your respective ages, you are hopefully well in to the no-bullshit phases of your lives.

/r/relationship_advice Thread