...his chats are pretty straightforward. Nothing that indicates a desire to cheat. He truly seems to be searching for a woman for a regular threesome. The problem is that I am questioning whether I want another woman in our life. I asked him why he is so obsessed with finding someone, and he simply said that it would be "fun and hot." Since he is much older than most men on these sites, women tend to pass him over. I have this fervent wish that he doesn't find someone. So do I sit back and hope that he doesn't find another woman, or should I be up-front with him and tell him that I'm not interested in threesomes anymore? I'm afraid that if he finds someone, my jealousy—which I work very hard to hide from him—will break us up. I am almost getting obsessed myself, checking the sites and his chats constantly. It is bordering on the ridiculous. What should I do?

Just Wants To Be Monogamous

My response after the jump...

Ask yourself which conversation will be more difficult:

A. After a frustrating and protracted search, your boyfriend finally manages to find a woman who's interested in being your "friend and lover," JWTBM. At that point, you tell him you're no longer interested in a third, regular or otherwise, and he needn't have bothered.

B. You tell your boyfriend today—now—that you're not interested in bringing a third into the relationship, regular or otherwise.

It's the same conversation either way, JWTBM: You're gonna have to tell him you're not interested. Don't count on him dying before he manages to find someone; he may be too old for the women on the websites he's haunting now, but sooner or later, either he'll find his way to a website where his age isn't an issue, or a bi woman into older men will stumble over one of the ads he already has up. So you're going to have to tell him the truth, JWTBM, the only question is when.

I would argue that having the conversation now would be preferable to having it after he's set up a date for drinks with a potential third. He may be disappointed to learn that you're not interested in a third anymore, JWTBM, but he's less likely to be breakup-level angry/hurt if you didn't stand there silently while he wasted time searching for a third.

And who knows? An honest and open conversation about the state of your relationship—including the fact that you're dissatisfied with the once-a-week routine and the waning of D/s—may ignite an interest in a third. Would you feel differently about a third if it turned out she wasn't for him (so nothing to be jealous about), JWTBM, but for you? He's getting older, he has health issues, and he may want someone else around so that you won't leave him to get your needs met. It's also possible that a third would reignite the D/s dynamics that you miss. D/s is performance, it's play, and nothing invigorates a pair of performers quite like a new audience.

I'm not telling you that you have to agree to the third—if it's monogamy you want, then it's monogamy you should ask for—but keep your mind, your options, and those lines of communication all open.