I'm on hiatus while working on a manuscript for a new book. In the meantime, please enjoy these classic Savage Love letters pulled from previous columns. I will be back October 1st, when the book is finished. —Dan

Originally published Oct 1, 2009:

Two of my closest friends, a straight couple, recently got engaged. As an engagement present, my female friend would like to include me in their sex life, potentially for just one evening or perhaps for longer. She and I have had a few make-out sessions while her fiancÉ watched, and I am somewhat turned on by the idea of taking our escapades further. But there's a catch: I'm currently seeing someone who says he doesn't consider hypothetical situations like this to be "cheating" but would probably be uncomfortable if I actually did this for my friends. Should I tell my friends I can't go any further out of respect for his feelings, or tell him that the situation is no longer hypothetical and risk making him uncomfortable, or help my friends out on the condition that it only happens once and not tell him at all?

Toying With A Third

My response after the jump...

Well aren't you the selfless little people-pleaser, TWAT. You're willing to sleep with this couple—maybe once, maybe weekly—even though you're only "somewhat turned on by the idea." But if you "did this for [your] friends"—if you condescended to help them out—what do you tell the man you're currently seeing? You could tell him the truth, of course, which would be the right thing, the responsible thing, the ethical thing—but that might make him uncomfortable, poor dear. So you hesitate. Oh, not out of selfish desire to avoid an awkward conversation, of course, just out of an overabundance of concern for his feelings.

Sorry, TWAT, since your boyfriend has already given you his hypothetical okay to get with your friends, there's no way to justify making an engagement present of yourself without informing him in advance. And let's be honest, shall we? Your reluctance to inform the boyfriend isn't about a selfless desire to spare his feelings, but your cowardly desire to avoid an awkward conversation and—if he balks at this hypothetical becoming a reality—a potentially relationship-ending conversation.

But before you can be honest with the boyfriend, TWAT, you're going to need to be honest with yourself. Repeat after me: "Honey, remember that couple, my insanely hot friends? They've asked me to have a three-way with them and I want to so bad my ovaries are throbbing—that cool with you?"