I don't want to become one of those people who writes to you complaining about how I married someone I wasn't sexually compatible with 10 years ago and now my sex life still sucks. I already know I need to break up with my boyfriend, and I was about to do it when he got sick with the flu. This was at the beginning of March. I assumed he'd be sick for a week and then we would have an unpleasant conversation. But then the entire country shut down and my boyfriend was officially diagnosed with COVID-19. So I haven't seen him since the last weekend in February—Monday was Memorial Day, Dan, in case you've lost all concept of time—and I've been playing the role of the supportive and worried girlfriend from afar. But it's been hard. Both my parents are in high-risk groups and my mental health has been battered. My boyfriend is finally getting better and I don't know what to do when I finally have to see him again. I'm not breaking up with him because he's a bad person, and I don't want to hurt him, but that's exactly what's going to happen. I feel guilty because I'm choosing my happiness over his. I know I shouldn't, Dan, but I do. —Feeling Resentful About Uncoupling Dilemma
Pandemic or no pandemic, FRAUD, you can’t stay with someone forever—you can’t be miserable for the rest of your life—to spare that person the routine and surmountable pain of getting dumped. Not breaking up with your boyfriend while he was fighting COVID-19 was the right thing to do, of course, and I don’t for a minute question the sincerity of your concern for him. (You want to see the relationship end, FRAUD, not him.) But don’t wait until you see him again to break up with him. It’ll suck for him, of course, but the world is full of people who got dumped and got over it. And the sooner he gets over you, the sooner he’ll meet someone else. For all you know he’s been chatting over his backyard fence—at a safe distance—with a neighbor he would be interested in dating if he were single.
For the past few months my GF and I have been quarantined together. Except for the time we've spent working, we're constantly in each other's company and doing things together. It's been great so far. It's good to know that we won't get tired of each other or feel smothered. The main problem is finding something to watch or something to do. Any suggestions? —Quarantined Until
I’ve been reading “The Mirror and the Light,” the final installment of Hilary Mantel’s epic account of the inner life of Thomas Cromwell, Henry VIII’s most powerful minister—the guy who arranged for the beheading of Anne Boleyn—while listening to whatever classical music my husband puts on. But just so you don’t think it’s all award-winning fiction and high art where we’re quarantining, we’ve also been watching “90 Day Fiancé,” which is a complete (and completely engrossing) shit show, and “The Simple Life” with Paris Hilton and Nicole Richie, which I missed when it first ran. So obviously I would suggest fiction, music, and crap television—and anal, of course.
My problem is that I am seriously worried about missing out on life. I’m a man. I find men attractive but I have no idea how to get to know one. For the first time last summer I met someone and we were sexual with each other. He was a hockey player. But he is gone now. And when I try to be friendly with other men, I get called out for flirting. I am gay and don’t know how much hurt I can take. —Making All These Connections Hard
More than 80% of gay relationships got their start online before the pandemic began, MATCH, and that number is surely higher now. So if you got on gay dating/hookup apps instead of flirting with random men, you would be talking to a self-selected group of men who are inviting other men to flirt with them. You’ll still face rejection, of course, and you’ll still get hurt. To live is to suffer, as some philosopher or other once said, but the suffering is easier to bear if you’re getting your dick sucked once in a while.
I'm 34, nonbinary but presenting female. Due to a series of personal tragedies (death, deportation, illness—it was not a Top 10 year), I'm sheltering with my parents. Long story short, I'm 100% financially dependent on my parents right now. The upside is, I've had a lot of time to become comfortable with the fact that I really, really want to mess around with cross-dressing. I would love to get a binder and a masc get up and haircut and just see how that feels. My parents will want to know "what this means" and they won't take "fuck if I know" for an answer. It will be a long time (maybe years) before I'm either eligible for disability or ready to work again, and I just can't wait that long. So much of my life has already passed me by and I'm tired of waiting for a "right time." But binders and clothes and haircuts cost money. Keeping masc stuff around the house means people will eventually see it. Again, they'd probably be supportive, but I just want to keep this private. Is there a way to do it? —Hoping For A Third Option
Other than winning the lottery and moving out on your own tomorrow, HFATO, there’s no third option here. You’re going to have to pick your poison: risk having an awkward conversation with parents who are likely to be supportive or continue to wait—possibly for years—before you start exploring your gender presentation. The choice seems obvious to me.
Got in an argument recently about pegging and its original definition: "a women fucking a man in the ass with strap-on dildo.” I feel it’s moved beyond that and now means anyone wearing a strap-on fucking anyone else in the ass. My friends insisted that only a man can be pegged, and only by a woman. As the originator of the term, Dan, we turn to you: Can a woman peg another woman? —A New Ass Licker
I will allow it.
Are some people just bad at sex? My partner has been overwhelmed with work and our sex life suffered a major decline. He’s working with a psychotherapist who told him some people are just not good at sex and he should just accept that he’s one of those people. It broke my heart to know someone said that to my partner. Am I overreacting? Is there some way to take this as anything but wrong? Or is this therapist a clown? —Completely Undermining Negative Therapy
There are people out there who are “bad at sex” by objective measures. There has to be. But “good sex” is so subjective that I’m not convinced objective measures really matter. For example, I got a letter yesterday from someone complaining their partner is “bad at sex” because they just lie there, silent and inert, while the letter writer “does all the work.” But if the person who just lies there was partnered with a necrophiliac, well, that “silent and inert” stuff would make them great at sex, not bad at sex, at least by a necrophiliac’s standards. As for your boyfriend, CUNT, you’re in a better position to judge whether he’s good at sex—by your subjective standards—than his shrink. Presumably. And if you enjoyed the sex you were having before your partner was overwhelmed with work, then he’s good at sex—he’s good sex by your standards—and here’s hoping you get back to having lots of good sex together soon.
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