Dear Dan: I’m a single gay male in my 40s. I have a good life and do good work. I’m not worried about finding the right guy to settle down with. I’m worried about what happens next. I’ve had three serious long-term relationships and several friends-with-benefits relationships. In every single one, a time has come, generally sooner rather than later, when I completely lose interest in my partner sexually. It’s not a matter of him being less attractive to me. It’s not a matter of us not being on good terms — often we become very close friends. It’s not a matter of my sex drive shutting down — I’m all kinds of turned on by other guys, just not the one I’m with. It’s reached a point where I’m deliberately holding myself back from getting into relationships because I’m tired of ruining good things. — Confirmed Bachelor
Dear CB: You could get your ass into therapy, CB, and churn through several relationships while you work on this — relationships that could fail for this or some other reason — and not have anything to show for your effort 10 years from now. Or you could find a guy who has the same problem you do — your predicament is not uncommon — and instead of breaking up when you lose interest in each other sexually, you stay together, you love each other, you take care of each other, and you both fuck other guys.
Dear Dan: Mid-20s female here, ready to date after a period of difficulty in my personal life. I have started taking an antidepressant, which has allowed me to regain control over my life, but one side effect is difficulty having orgasms. People can be judgey when it comes to antidepressants, and it’s not something that’s easy to share. It’s frustrating because this medication allows me to be in a place mentally where I can pursue healthy adult relationships, but it affects sex, which for me is something that is key for a healthy relationship. How do I have a conversation about this with a potential partner?
— Hopeful About Potential Partners, Yay
Dear HAPPY: You can put off the convo about your meds with a white lie, HAPPY, by telling your potential partner you never come the first few times you’re with someone new — no pressure on you to come (or come clean just yet), no pressure on them to make you come. Then level with them about the real reason you’re having difficultly coming — new to antidepressants, still adjusting, but grateful for the other benefits — after you’ve gotten to know them better. It’s a harmless, understandable white lie, not a major betrayal. If they react like it is one, HAPPY, then you’ll have to DTMFA.
Dear Dan: I’m male, 30, and newly single. I’ve been using my newfound freedom to sleep around, and last week I had sex with a married woman. Yes, she was cheating. Yes, I was aware. There won’t be any future sexual encounters with this woman, but here’s the thing I was wondering about: I don’t feel guilty, not one bit. This fuck was a strong contender for best fuck of my life. Does that make me a bad person? And if so, do I just accept the fact that I’m a bad person?
— Basically A Dastardly Dick, Yes?
Dear BADDY: Fucking someone you know to be cheating implicates you in an infidelity, of course, and that’s usually bad — but not always. In some cases, cheating is the least worst option for all involved (the cheater, the cheated, their dependents); in others, cheating saves marriages that needed saving; in still others, cheating ends marriages that needed ending. Absent more info about this woman’s particular circumstances, BADDY, I can’t make a definite ruling about her badness for cheating or your badness for aiding and abetting.
Dear Dan: Straight 64-year-old man wanting to try the gay side of life!!! Don’t have the bodybuilder’s body anymore!!! Average size!!! Would anyone get turned on to old-timer’s body!!! Need some advice where and how to meet other gay men!!! Also HIV is a concern!!! Any other advice would be appreciated!!! — When I’m Sixty-Four
Dear WISF: Check out daddyhunt.com, WISF, the “largest gay personals site for daddies, bears, and guys that love them”!!! Don’t be paralyzed by fear!!! Of HIV or anything else!!! But consider getting on PrEP!!! And use condoms!!! And remember::: Sex with a guy who thinks he’s negative but isn’t is way riskier than sex with a guy who knows he’s positive and takes his meds!!! And stop calling yourself straight!!! Send questions to firstname.lastname@example.org and follow @fakedansavage on Twitter.