Q: I’m a 43-year-old straight woman, and I spent the majority of my 30s celibate. At 40, I realized that while I wasn’t interested in dating, I was tired of my vibrator. I also realized that it was time to go forth and fuck with the body I had instead of waiting for the idealized body I was going to have someday. Over the past three years—despite being as fat as ever—I’ve consistently had fun, satisfying, exciting, creative, sometimes weird, occasionally scary, but mostly awesome sex. One guy I met on Craigslist was particularly great: awesome kisser, amazing dick. He came over, we fucked, it was excellent, we chatted, he left. This happened about four times. And then CL shut down the personals section. The only contact info I have for the guy is the anonymous CL address, and it no longer works. He has my Gmail address (the one I use for dating sites), but he has not e-mailed me. I’m not a crazy stalker (I swear!), but he once told me he teaches at a university in our area, and I managed to find his photo and contact info on the school website. So I know how to reach him—but that’s a spectacularly bad idea, right? Unless you think it isn’t? If a dude I’d fucked a few times tracked me down at my job, I would freak out. But I keep thinking: Would it really be SUCH a bad idea to send him ONE e-mail? Should I just accept that it was great while it lasted? Or should I e-mail him and run the risk of pissing off/freaking out a nice guy? —Can Really Envision Every Possibility
A: Don’t do it, CREEP—don’t do that thing you already know you shouldn’t, that thing you wouldn’t want some dude to do to you, that thing you were probably hoping I’d give you permission to do.
That thing? Don’t do it.
You’re engaged in what’s called “dickful thinking” when guys do it—at least that’s what I call it, CREEP. It’s like wishful thinking, but with dicks. Men convince themselves of something improbable (“I bet she’s one of those women who like unsolicited dick pics!”) or unlikely (“Showing up at her workplace will convince her to take me back!”) because it’s what they want. Think of all the guys you’ve ever known who said, “She wants me!” when in reality he was the one who wanted her. Clitful thinking may be rarer than dickful thinking—women being less likely to think with their genitals and/or being more risk-averse due to socialization, slut-shaming, and the ever-present threat of gendered violence—but it’s not unheard of for a woman to rationalize unacceptable behavior (contacting this man at work) or deploy a self-serving justification (it’s just ONE e-mail) or solicit a “You go, girl!” from a sex-advice columnist when what she needs to hear is “Hell no, girl!”
Again, don’t do it. This guy has your e-mail address and he knows how to reach you. And since you didn’t have all that fun, satisfying, exciting, creative sex over the last few years with only him, CREEP, I shouldn’t have to tell you to focus on your other options. But since your clit is doing your thinking for you right now, I must: Leave this dude alone and go fuck some other dudes.
Q: I have a desperate question for you. I’ve worked with a vivacious 30-year-old for five years. For three and a half years, she had a live-in boyfriend. She had a different boyfriend recently. I’m 58 years old and not good-looking. She is always sweet to me and always compliments me. She’s said that I’m a genius and a gentleman, that I’m a hoot, and that I have a confident walk. I’ve also overheard her say that she likes older men. However, a few months ago she walked up to me out of the blue and said that she just wants platonic relationships with coworkers. Then I overheard her say to another coworker: “I put out a sign, he will figure it out eventually.” But which sign did she mean? The “platonic” thing or the constant kindness? —Wondering On Reciprocated Kindnesses
A: This probably isn’t what you wanted to hear either, WORK, but this woman isn’t interested in you—and if you weren’t engaged in dickful thinking, you’d know that. But your dick has somehow managed to convince you that you’re the “he” she was referring to when she talked about sending someone a sign. But you need to ask yourself—and it’s best to ask right after you masturbate, as that’s when we’re least prone to dickful thinking—which is likelier: she went out of her way to let you know she’s not interested in dating anyone at work and you’re the “he” she was referring to, or the “he” she was referring to was one of the roughly four billion other men on the planet and not a coworker? I don’t mean to be cruel, WORK, I just want to stop you from doing something that could get you fired or screw up what has, up to now, been a pleasant work relationship. While kindness can sometimes signal romantic interest, the full weight of the evidence here—including the fact that she didn’t send an unambiguous signal when she was briefly single—indicates otherwise.
Q: I’m a cis, white, gay male—partnered 15 years, monogamous for the first 14. About a year ago, my partner agreed to let me play on my own outside of the relationship. The rules: not when he’s in town, no one comes home, no regulars. I’ve taken good care of myself (sexual frustration + gym)—and at 50, I find that I’m attracting guys half my age. Sometimes, in the heat of passion, they call me “daddy.” This took a LOT of getting used to, but am I going to stop what we’re doing to discuss nomenclature? Anyway, I refuse to call them “son,” because I find that creepy. “Baby” doesn’t really work for me, either—it’s what I call my partner. That leaves “boy.” Which is fine if they’re white. The problem is, some of the jaw-droppers calling me “daddy” have been Black. And I absolutely refuse to call a Black guy “boy.” I want to leave them feeling amazing, not brooding on race relations and power imbalances. So what does a beautiful, dark-skinned, daddy-loving young man want to be called by the older white guy pounding him? —Daddy’s Uncomfortable Race Relations
A: Good for you for being able to think clearly even when your dick is hard—even when it’s buried in some hot guy—but I have to fault you for not reasoning your way to the obvious answer.
You’re a white guy who doesn’t feel comfortable calling a Black sex partner “boy,” which is usually what gay guys who call older partners “daddy” want to hear. But instead of asking the Black guys you’re fucking what they want to be called, DURR, you opted to ask some other old white dude what he thinks the Black guys you’re fucking might want to be called. Do you see the problem here? The guys you should be asking about this . . . are the guys you’re fucking. And you don’t even have to call a halt to the action in order to ask them! Next time you’re balls-deep in some hot guy and he says, “Fuck me, daddy,” growl and say, “That’s right, I’m your daddy—and what are you?” If he says, “I’m your boy,” then that’s obviously what he wants to be called. v
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