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Ready to date, now what? 

Whether you’re a twentysomething teacher or closeted 64-year-old gay man, it’s totally possible! Dan shows you how.

Q I'm a 27-year-old straight male and a high-school teacher held to a strict code. I left my fiancée in June and haven't had sex since. Needless to say, I'm really horny. I'm also in that weird in-between age where I'm not comfortable hanging out at college bars but I'm also a bit younger than most of the women in other bars. But when I scour dating apps, I see profiles of women ages 18 to 22—women who, for all I know, could have been students at my school. I would never fuck a former student, of course, but I'm worried that I could get my license revoked if my supervisors discovered I was online trolling for sex. So what am I supposed to do? My cock is making sad faces at me right now. —Teacher Evidently Needs Sexual Encounter

A If you live in a college town, TENSE, there's at least one bar where grad students hang out—look for the bar where women are grading papers, not pounding shots, and hang out there. And with more than one in three new marriages beginning with an online meeting these days, and with Pew Research telling us that 60 percent of Americans approve of online dating, I don't see how your supervisors could possibly object to staffers scouring dating apps and the interwebs for age-appropriate partners.

Q I'm female, 26, and in an open marriage with a wonderful man. I am having a recurring fear that he'll get some other woman pregnant and she will refuse to abort. I trust him, but condoms break (or get holes poked in them). He inherited serious money from his father, and his father got "oops'd" into having three kids. I would immediately divorce my husband if this happened. (Yes, I'm an asshole, but my life plans have NEVER included children, step or otherwise.) My solution is for him to get a vasectomy. He says he's for it, but it's been a YEAR and he hasn't made an appointment. I'm seriously considering yanking "open" until he's sterile. Maybe he really wants children and he's not telling me, but I keep asking and he keeps saying no. Am I being unreasonable asking for the snip? —Seriously Not Into Pregnancy

A Maybe your husband wants children, SNIP, maybe he doesn't. Or maybe he's one of those guys invested in/aroused by the power of spunk to make babies they don't want; these guys would rather see their shots intercepted than go unattempted. So while a vasectomy is an eminently reasonable way for a married man who wishes to remain childless to prevent himself from impregnating someone who isn't his wife, SNIP, arousal often defies reason. And ultimately this is his decision to make–his body, his choice.

Q 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

A 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, stay together, love each other, take care of each other, and both fuck other guys.

Q 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 key for a healthy relationship. How do I have a conversation about this with a potential partner? —Hopeful About Potential Partners, Yay

A 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.

Q 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

A 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!!!

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