Q: I am a guy in my 40s, handsome, more financially successful than most, and a classic sexual scoundrel. I cheated on my ex-wife and every girlfriend I’ve ever had. I’m currently dating a woman in her 20s. We are both each other’s ideal type. She has as scandalous a past as I do but has “accomplished” more in a shorter time. We met via a hookup app. Then another one. And another one. We enjoyed each other’s company from the moment we met, and the sex was great. (We share a few not-easy-to-match kinks.) Most of her stuff is now at my house. We’ve had many deep dives into our respective pasts. We cringe now at how we met and why we’ve hooked up with so many random people. Here’s the issue: After 12 months together, with too many breakups to count, we have no idea how to move forward. We cannot establish trust. We are in love and everything’s great… so long as we have our eyeballs on each other. Once out of direct sight, we both turn into possessive assholes. So many phones have been stolen and thrown away, I can’t count. How do two sluts find peace?
—Can’t Part Over Sex
A: You’ve cheated on everyone you’ve ever been with, and your girlfriend has presumably cheated on everyone she’s ever been with. (That’s what you meant by “she has as scandalous a past as I do,” right?) But instead of embracing the cheats and sluts you both know yourselves to be and thanking your fucky stars for bringing you together, CPOS, you felt obligated to disavow your past behaviors—some of which sound legitimately terrible—and slut-shame yourselves and each other. And for what? You are still the people you were before you started theatrically cringing about how you met.
She doesn’t trust you not to cheat on her, and I don’t see why she should. You don’t trust her not to cheat on you, and I don’t see why you should. So why promise not to cheat? Why waste time and emotional energy policing each other for evidence of what you both know to be true: You’re going to cheat on each other. That you can trust in. So instead of making promises you can’t keep and then having meltdowns and stealing each other’s phones and breaking up and getting back together, CPOS, make a promise you can keep. Not to be faithful but to be considerate. And discreet. Promise not to do anything that makes her feel like she isn’t your top priority even if you do fuck around occasionally, and ask her to make the same promise to you. Then you can move forward as honest sluts and not lying cheats.
Q: I am in love with a happily married woman. I was the “other man” almost 20 years ago, before she was married but when she was living with the man she’s with now. We fell madly in love, but we didn’t end up together. In the intervening years, we both married and had children. We’ve reconnected a couple times over the years and it became a sexual relationship again. Here’s the tricky part: My then-wife was an undocumented immigrant. My marriage was unhappy, but for my child’s sake I couldn’t leave my wife, for fear of his mother getting deported. This year, she got her green card and we divorced. Then I reconnected with my ex again. We desperately want to get married, but she is scared to end her marriage. She’s in a relatively happy marriage, and divorce will be a bombshell. She worries about the shock and destabilizing effect on her children, who are still young. And she fears that nothing short of admitting she’s in love with someone else could end her otherwise happy marriage, but admitting that she’s been unfaithful will make co-parenting impossibly hard going forward. We agonize over this situation but can’t bear the thought of not being together. We understand that pain will have to happen, but we just don’t know what the best course of action is.
—Pensive And Incredibly Nervous
A: If you two can’t wait until her kids are a little older before you marry, PAIN, then there’s no way to avoid the most painful possible version of this shitshow. But your girlfriend’s husband deserves the whole truth right out of the gate, even at the risk of complicating their co-parenting arrangements in the short run. Letting her soon-to-be-ex-husband twist in the wind wondering why his decent, loving, seemingly stable marriage suddenly collapsed would just be cruel—and pointlessly so, as he will inevitably learn the truth. You two don’t plan to marry in secret, right? Which means her soon-to-be-ex and their kids are going to find out about you, the new husband and stepfather, at some point in the very near future. The whole truth, all at once. Don’t draw it out. Inflicting pain on the installment plan won’t assuage your guilt.
Q: I’m married to a loving, handsome man. For the first several years of our relationship, we had amazing sex. At some point after moving in together, my interest in having sex with him decreased significantly. This has been a pattern in every long-term relationship I’ve ever had. Living together seems to diminish my attraction to my partner, which is hugely problematic when I am in a long-term monogamous relationship. The second problem is that my kink needs are not being met. My husband is aware of my kinks and is GGG in theory, but he lacks the skill to deliver what I’m interested in. Before I met my husband, I spent many years as a member of a very active kink scene in a big city. I miss the friendships and experiences I had when I was able to share my kinks. Unfortunately, in addition to living in a place without access to these kinds of events and workshops, my husband is monogamous without compromise. He is unwilling to co-top me alongside another Dominant partner and unwilling to let me bottom for others solo regardless of whether sex is involved. Within the past several years, this frustration has led me to seek out the occasional experience with others, which is always discovered. My sex drive seems intact when I fantasize about hot, rough scenes with other people, but I experience very little desire for my husband. I’m at a loss. I adore this man, and haven’t ever felt like it would be worth it to leave him just so I could get my kinky needs met, but we are at an impasse. Is it even possible to find a compromise?
—Sex Alacrity Diminished
A: Knowing what you do about yourself—your attraction to a partner craters after moving in together, you have a powerful need to explore your kinks with casual play partners—you shouldn’t be cohabitating and/or making monogamous commitments. But you are and you have, SAD, so what now? There’s no middle ground between an uncompromisingly monogamous marriage and the kind of freedom to explore your kinks that you need to feel fulfilled, partnered or not. But your husband caught you fucking around—or kinking around—and has presumably forgiven you, seeing as you aren’t e-mailing during your divorce proceedings. So perhaps if given a choice between letting you and losing you, SAD, he would let you. And who knows? If all your long-term relationships have been monogamous, and they all resulted in the end of rough and adventurous sex with new partners, well, perhaps that’s what is cratering your desire for committed partners—the limitation, not the cohabitation. And who knows? If you were free to fuck around with other people—if your husband didn’t symbolize the end of sexy adventures—maybe you’d still want to fuck him. But if he does give you the freedom to fuck around and you still don’t want to fuck him, SAD, do your husband a favor and leave him. And then no more monogamy or cohabitation for you, got it?