Q: I’m a guy, 35, and a cheating piece of shit. I’m engaged to a woman I love, but earlier this year I cheated on her. I have no excuse. She discovered the dating app I used, and we worked through that. But she doesn’t know that shortly after her discovery, I went ahead and cheated. To my meager, meager credit, I did seek out only women who were looking for NSA hookups. But I quickly came to realize how big of a mistake this was, how much I love my fiancee, and that I’m a shitty person. I see a therapist, and he advised that, if I’m certain this was a onetime thing, and if I’m convinced that I’m happy with my fiancee, I should keep quiet. I shouldn’t burden my fiancee with this knowledge. I’m inclined to agree but, dear God, the guilt. I feel like I’m not the person my fiancee thought I was. What do I do? Should I just accept this as a lesson learned and keep it to myself? Perhaps there’s selfishness at play here, since I’m trying to make myself feel better, but I’m struggling. —Can’t Personally Overlook Selfishness
Q: My boyfriend of five years is a sweet, smart, handsome, loving, supportive, middle-aged, chubby white guy. We have a fulfilling sex life. When we first met, he shared a fantasy he had about watching me get fucked by a black guy. (He knows it’s not something I’m interested in IRL.) I’ve caught him several times posing online as a young, buff, handsome black guy looking for a “snowbunny.” I call him out on it every time, and it causes huge fights. He says he’ll stop, but he never does. Weighed against all his other good qualities, this isn’t that big of a deal. Clearly he’s not going to meet up with the women he’s chatting with. What makes me sad is that I adore him as he is—I love his big white belly, his bald head, and his rosy cheeks. I think I do a good job of communicating this to him. I guess I’m writing to you for some reassurance that I’m doing the right thing by letting this behavior go and also for some insight into why he’s doing it in the first place. —Upset Girlfriend Hates Eroticized Racial Secrets
Q: I am a 36-year-old Italian straight man. I love my girlfriend endlessly. One month ago, she told me she has thoughts about missing out on the things she didn’t get to do in her teens. She is 29 years old now. Also, she says she feels only a mild love for me now and is curious about other men. Yesterday we met and cried and talked and made love and it felt like she still loves me passionately. But she also told me she had sex with a stranger a week ago and she is going for one and a half months to Los Angeles on her own. Now I feel confused. I should hate her for what she did to me, I should tell her to fuck off, but I can’t do it. I am so in love and I want to be together again after her trip. How do I exit this turmoil? —Pensive and Insecure Now
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