My boyfriend wants my permission to see sex workers. He did this quite a bit before we were together. He goes to Canada, where it’s legal and supposedly safer. He says he’s just trying to be open and honest about his desire for variety and that I should be glad he doesn’t want to cheat. To me, that sounds like a thinly veiled threat to cheat with or without my permission. He says it’s not like that. Ideally, he — a 56-year-old man — would prefer a sexually open relationship, while I — a 48-year-old woman — would prefer more of a monogamish situation.

We were friends for twenty years before we started dating, we have great sex (though not as much as I would like), get along wonderfully otherwise, and have a lovely time together. This is definitely our biggest issue. Am I being closed minded, and prude to deny him the variety he desires? I consider myself pretty open minded, but I am triggered by this. I’m not closed to adventures. I’m open to threesomes, sex parties, etc., but those are scenarios where we are doing something together. I’ve been in non-monogamous relationships in the past — consensual ones — but I don’t have the energy for that at this point in my life.

Safety concerns aside, I have moral hang-ups around sex work. All I can think is, “What self-respecting woman would put up with this?” The other thing is that he has a long history of dating much younger women, sometimes as much as twenty years younger. I may be the first “age-appropriate” girlfriend he’s ever had. While I know I am still very attractive and sexy and I get hit on all the time, the reality is that I will never be young and firm again. The ones he hires are both of those things. Are we doomed? Can we both find fulfillment in this relationship? Or should we let each other go?

Verklempt In Vermont

A particular phrase came to mind as I read your letter, VIV, but it won’t come as a comfort: irreconcilable differences

You can’t reconcile yourself to your boyfriend seeing sex workers; your boyfriend can’t reconcile himself to monogamy and/or the kind of non-monogamy you might be willing to explore… if you were interested in exploring non-monogamy… which it doesn’t sound like you are. While sex parties, swinging, threesomes, and other forms of non-monogamy where the couple plays together appeals to you in theory, VIV, none of that seems to appeal in practice. And if you told your boyfriend what you told me — you don’t have the energy for non-monogamy anymore — he may fear the promised sex parties and threesomes may never materialize. So, for variety’s sake, he’d rather get your permission to make something happen for himself (seeing sex workers on business trips) than wait on things that might never happen (attending sex parties with you). It’s also possible your boyfriend prefers sex one-on-one — with you and other partners — over the kind of group play you might be willing to explore.

Which means you two are at an impasse. Your boyfriend needs a particular thing to be happy — a permission slip from his partner to see sex workers — and you need the opposite thing: not just a promise from your partner to refrain from seeing sex workers, but ideally a partner with no interest in having sex outside the relationship at all.

And he’s not that guy.

If I may paraphrase Maya Angelou: when someone drops unambiguous hints about who they are, take the hint the first time. While your boyfriend didn’t explicitly say he’s incapable of honoring a monogamous commitment, he made it pretty clear that he’d rather not be bound by one. I think the tell here, VIV, is that he said seeing sex workers with your permission was a better choice than cheating while failing to include not seeing sex workers on his short list of possible options.

So, is this relationship doomed?

Read the rest of this week's column here!