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: 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 shit show. 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.
