Dear Uncle Gary, After seven years of monogamous bliss, my partner Mike, two years older, two inches taller, and apparently two egos too many, decided it was time to “open things up.” Not emotionally. Sexually. To other men. Now, I’ve always been a one-dish kind of diner. I don’t like to share my fries, let alone my boyfriend. But after weeks of pillow talk negotiations and a few glasses of wine, I agreed to try it. Spoiler: I did not love it. Mike, bless his biceps, is a big

Dear Uncle Gary, I’m five months postpartum with our second child, and I’ve been carrying around about 40 extra pounds from the pregnancy. Things have been tender and exhausting, and intimacy with my husband has all but disappeared. He never initiates anything anymore. The few times we’ve had sex since the baby came, it was because I initiated sex. This morning, something strange happened. A package arrived in the mail, no return address, just a plain brown envelope with gene

Dear Uncle Gary, I’m a 65-year-old woman who’s been divorced for over a decade. I raised two kids, built a career, and now I’m retired with a little house, a garden I love, and more quiet than I know what to do with. Here’s the thing. I’m not lonely exactly, but I do miss being touched. Not just sex, though I wouldn’t say no to that either, but the little things. A hand on my back. Someone brushing hair out of my eyes. That feeling of being seen and wanted. I’ve tried dating

Dear Uncle Gary, My best friend just got engaged, and I am genuinely happy for her. But every time I hear her talk about the wedding, I feel this weird mix of joy and jealousy. I am single, I have not been on a real date in over a year, and I keep wondering if something is wrong with me. I do not want to be bitter, but I also do not want to pretend I am not struggling. How do I show up for her without losing myself in the process? Signed, Third Wheel with a Smile. Dear Third

Dear Uncle Gary, I recently started dating a guy who’s sweet, smart, and has the kind of jawline that could slice deli meat. But here’s the thing: he claps when the plane lands. Every time. Loudly. With enthusiasm. I tried to ignore it, but last week he stood up and said, “Great job, Captain!” like we were at a Broadway curtain call. Is this a red flag, or am I just being petty? Signed, Turbulence in Aisle 3 Dear Turbulence, First of all, let’s take a moment to honor the jawl

I'm recently out of a twelve-year relationship. I'm a fifty-five-year-old gay man, and I don't know where to start. I used to have a nice body. I think I'm still good-looking, but when I go out with friends, I never meet anyone. Everybody is so young. Signed, Need A Bear Hug Dear Need A Bear Hug, First of all, I’m going to gently suggest we retire that nickname. You’ve been through a twelve-year relationship, that’s a lifetime of shared routines, inside jokes, and probably a