The Friends With Benefits Vacation
My question is RE: relationship etiquette involving a “friends with benefits” arrangement.

Dear Rob,
My question is RE: relationship etiquette involving a “friends with benefits” arrangement.

I have a female friend with whom I have a mutually beneficial (not financial) arrangement, in which she receives some actual benefits and in return we have regular “dates”.

I am not asking re: the morality of that type of arrangement, but simply about the limits and expectations from either of us.

Specifically, if I take my friend on a vacation trip for which I pay for everything, airfare, hotel, side trips, etc. is it reasonable for me to expect to have sex with her while on the trip??

Secondly and related, is it “OK” for either of us to seek or meet other potential partners while on this same trip??

I think that you are confusing a “friends with benefits” arrangement to one of having a woman available any time you’re ready for her, and providing for her, to have sex with her.

I hate to be brutal but from what you wrote me sounds more like you “give” her things in expectation of sex.

But you don’t want a lesson about morality, so here goes:

Specifically, if you take her on a vacation you are her “date” for the duration of that trip.

I don’t think it is reasonable to expect sex but at the same time I don’t think that either of you should go to the hotel bar and pick up a “new friend” for the evening.

And based on my answer above, unless the both of you agree together that this is an “open” vacation, there should be no mingling with other people looking for a sexual side-adventure.

After all, maybe you can’t get some side action but she can… how do either of you feel about this happening?

I know that if I was footing the bills I wouldn’t want to get “shut out” at the end of an evening and I wouldn’t want the responsibility of her feeling rejected haunting me from the first night out should I get lucky and she doesn’t…

And what if she gets to have the fun of her life but you get sidelined… and she’s not even around for comfort and you hurt all the more?

And what else could happen to totally ruin an otherwise fun trip when two people go as “singles” but still have “expectations” of a “pseudo-sexual relationship” without conditions or responsibilities.

To sum up… this is a bad idea unless you’re both on the same page for the trip, you both have the same understanding and expectations of behavior.

“Friends with Benefits” always has a crushing point where the idea of the relationship leads for more expectations on one person than the other.

You are at the crux of failure and abandonment. Expect less and enjoy more. Keep the rules in the open with no second guessing.

And expand your circle of friends…. I am sure she is doing that on your tab.
Best wishes,