I’m a gay man in his early 30s who’s into sex stripped down to its most basic elements: tops come in, fuck me, come and go. I’ve moved to a new city. One guy in his mid-twenties came over, and we had awkward but passionate sex like that. We chatted a little afterward. I went to his apartment to see him a week later, and we did it again. It was hot; we had chemistry. Turns out, he’s also new in town. He’s from a conservative part of the country and says I’m the second man he’s ever had sex with. He’s got a lot of things I look for in romantic partners: smart, cute, soft-spoken, driven, and into his job. The bad part is that he’s in management training for a problematic fast-food company, and while he’s fairly apolitical, he says he will “probably” vote for Trump.
While there are certainly plenty of gay conservatives, I feel like he’s someone who hasn’t seriously given a lot of thought to politics outside of his strong belief in free enterprise. This isn’t someone who thinks a lot about intersectionality or who has interrogated the way capitalism exploits. He wants to be a good boss. You said once not to fuck Republicans because they should go fuck themselves. But I feel like there might be something here I can draw out of him. At the very least, his desire for kinky gay sex might make him willing to hear me out about my sharply divergent politics. But I don’t want to entertain someone who just wants his cake (my ass) and the license to eat it (his abhorrent politics), too. But the sex is good, and I like the idea of fixing him. What to do?
Aroused Slut Sees Ultimate Potential
For decades, ASSUP, I have urged sane gay men not to fuck gay Republicans — gay Republicans can go fuck themselves — but in 2015, I singled out one gay Republican in particular that I didn’t want other gay men fucking: Tim Miller, former campaign staffer for John McCain, former spokesman for the Republican National Committee, and at the time of my tweet, communications director for Jeb Bush. Seeing as Tim is no longer a Republican (but still a gay man), and seeing as my position on fucking gay Republicans hasn’t changed (just say no), I thought Tim might be able to offer you an unbiased answer. Despite my having urged other gay men not to suck Tim’s dick (without effect, it seems), Tim graciously agreed to weigh in. His response follows…
Yo ASSUP.
As a former Republican who Dan once tried to cockblock on account of his political views — unsuccessfully, I might add (very unsuccessfully) — I appreciate where your head is. Your instinct is downright humanitarian. It’s in line with the message Barack Obama delivered at the DNC convention. No, not the dick joke, the part where he said, “Everyone deserves a chance, and even when we don’t agree with each other, we can find a way to live with each other.” And here you are giving this hate chicken middle manager a chance to live in you! It’s a beautiful instinct really. Who knows, with your vice grip on his dick, maybe this young gay conservative might blossom into a coconut-pilled podcast host who eviscerates any MAGA moron that dares cross his path like yours truly.
On the other hand…
It’s 2024, not 2014. Donald Trump attempted an insurrection. He’s currently advancing a racist conspiracy about black immigrants abducting and eating house pets. He is a worthless shart stain with no redeeming qualities or virtues and that’s been abundantly clear to anyone with a brain for at least nine years now. Being for Trump at this point… it’s not exactly the same as just mindlessly supporting Tom Tillis. It’s an act of active malice or supreme stupidity.
So, like you, ASSUP, I’m torn. Not a great quality in an advice columnist but unfortunately for you Dan passed your question off to a substitute.
I guess my ruling comes down to a practical calculation. If he lives in a swing state, hold your hole hostage until he pledges to support Kamala. We can’t fuck around with so much on the line. If he doesn’t live in a swing state, well, give it a few more whirls, at least until he reveals himself to be intentionally awful. Who knows what could happen, right? After all, we are the ones we’ve been waiting for, maybe your hole has the change he seeks. — Tim Miller
I wanna thank Tim — both for offering you some advice, ASSUP, and for eviscerating MAGA morons five days a week on The Bulwark’s flagship daily podcast — and I wanna officially lift my fagwa against his dick: gay men everywhere can suck Tim’s dick without incurring my wrath.
I also wanna expand a bit on something Tim said: can your hole — can anyone’s hole — change a person? While I think some people are too far gone for hole (or pole) to save (you can’t fuck the Nazi out of someone), some people don’t ever think critically about political beliefs instilled in them by rightwing families or churches until challenged by someone they’ve just fucked and wanna fuck again. There’s something magical about the combination of sexual attraction, limerence, and oxytocin, the “love hormone” that floods our systems during really good sex. When all three come together, ASSUP, it can open a person up in surprising ways. So, while it took the nomination of Donald Trump for Tim Miller to see the GOP for what it was (and Tim has gone on to do amazing and important work in the fight against Trump and Trumpism), for other former gay Republicans it was something a guy said to them during their refractory period — that moment when minds and asses gape open — that made the difference.
So, you have my blessing, ASSUP, to keep fucking this guy. But to assuage your guilt (and avoid my wrath), you should gently draw this man out about his politics (and his fast-food preferences) after he unloads in you. (There’s no better time to get someone to, um, interrogate the way capitalism exploits.) If thinking a little more deeply about his vote is the price he has to pay to keep unloading in you — if he knows he’s going to have to defend the indefensible when he sees you again — he may wind up voting for Kamala Harris along with you and me and Tim and all the other gay men out there with their heads screwed on straight.
You’ve got a little less than six weeks to fix this guy, ASSUP, so we’re gonna need you to douche daily and spend as much time in this man’s apartment — and on this man’s dick — as you can between now and November 5th. Your country is counting on you.
Tim Miller is the author of Why We Did It: A Travelogue from the Republican Road to Hell. Follow him on Twitter @timodc and Threads @timmillergram.
I’m a woman in my early forties, in what has always been an ethically non-monogamous marriage, with two middle-school kids. It’s my ex-friend’s/lover’s birthday today. My husband met her on Tinder, and we connected over the fact that we both survived a relationship with the same manipulative, controlling, abusive asshole. Our relationships with him — without our knowledge — were overlapping. He’s a “Dom” only in that he was willing to use BDSM to mindfuck us both, constantly bending the concept of consent. He lied to both of us and deceived every step of the way. Top-level Dark Triad dude. My relationship with him almost broke my family apart. My ex-friend said she has also hit the lowest point in her life because of him. Over the last three years, we helped each other heal while developing a small fun supporting tribe. Our kids became friends, we spent all our weekends together, went on camping trips, helped each other with house repairs. It was idyllic. Sex became a part of our relationship on her initiative. I made it clear that I didn’t want sex to be the main focus of our relationship. She agreed, but it soon became clear that she needed more from us — me and my husband both — than we could deliver. My focus was on the kids, hers and ours, and I always opted for activities that involved our families, while she preferred adult fun.
Then one day she told me she got back with the asshole. I was in shock. I felt betrayed. I could only tell her I couldn’t be in her life if he was her life too, and to get back to me when he was out of the picture. I haven’t heard from her in two months. Our kids miss their friends. I also feel bad for her, and I feel a need to help, but I need to maintain my boundaries. My husband cares too, but he’s extremely busy with his startup, so doesn’t really have the bandwidth. How should I navigate this? Should I reach out for the sake of all kids? I’m incredibly lonely and I miss her.
Mothers Experiencing Sensitive Situation
I think you should reach out to your friend — let’s not slap the ex-friend label on her quite yet — for your kids’ sake, MESS, but also for your own.
You were extremely close until about two months ago, MESS, when your friend made a choice that dredged up painful memories and struck at the foundation of your initial connection: you bonded over being jerked around by the same terrible man at the same terrible time and now she’s seeing him again But you miss your friend, MESS, and your kids miss their friends. So, again, for your sake and theirs, I think you should reach out to her.
Maintaining our boundaries is important, MESS, but sometimes we need to revisit and revise our boundaries. You don’t have to pretend to approve of what your friend is doing — you can and should express your disapproval — and you don’t have to let Mr. Dark Triad back into your life. But hearing from your friend about why she let him back into her life might give you clarity about what to do next. If she’s back in Mr. Dark Triad’s thrall and starts making excuses for him, you won’t want your friend back in your life the way she was before. But if you completely cut her off — if you refuse to even let your kids get together — you’ll be doing Mr. Dark Triad a favor, MESS, as you would be isolating your friend.
But it’s possible she isn’t in this thrall. A friend of mine once dated a guy who was a pathological liar. (He was in the CIA, he wrote for the Washington Post, his father owned the Dallas Cowboys.) My friend was in love with this guy and they were about to move in with each other when my friend came to his senses and dumped him. I was mystified six months later when they got back together. I felt better after talking to my friend: he wasn’t serious about this guy anymore — he was no longer in his thrall — and he was now able to take from him what he wanted (the sex was amazing) without taking him or anything he said seriously, as he no longer regarded him as a potential life partner. He didn’t have to pretend to believe his lies anymore and, more importantly, he didn’t have to defend his lies to his friends.
Now that your friend knows she can’t believe anything this man tells her — now that she knows he’s a manipulative asshole — he may not have the vice-grip hold on her that he once did. If she’s able to enjoy the dick (and the D/s) without being made crazy by his lies, getting together with this guy may not be putting her sanity at risk the same way it once did, even if it is — at the moment — putting your friendship at risk.
P.S. I’ve also watched friends get back together with deeply shitty exes and get burned — and burned badly — all over again. Some people have to touch a hot stove twice before they learn to stay the fuck away from it.
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