My boyfriend (31M) and I (24F) were talking about age gaps in dating. For context, we met when I was 22, and he was 29, so we have a gap ourselves. Before him, I’d only ever been in a long-term relationship with someone just a year older than me, so this dynamic is very different.

I’m a 26F married to a 27M. We’ve been together 8 years and have two young kids. Our relationship has had serious issues.

Dear Uncle Gary, I’m 19 and live with my parents. My brother (32) and his girlfriend, she’s either 21 or 22- I live about 15 minutes away, but they stayed with us this weekend for my dad’s birthday. My brother and I aren’t very close, and I haven’t talked much with his girlfriend, but she seems nice. We’re close in age, and we go to the same college, so I could actually see us becoming friends. (The age gap between her and my brother is a little weird, especially since she’s

Hey Uncle Gary, Twenty years of marriage. Five kids. Back in February I lost my job, and though I’ve recently found another in the same field, it came with a 50% pay cut. I was overpaid before, and the financial stress has been crushing. I’ll admit it, I haven’t been the best husband these past months, buried under the weight of being the sole provider. Meanwhile, my wife started going out three to five nights a week, coming home drunk more often than not. While I was away fo

Hey Uncle Gary, My mom (39) is dating her coworker (20). I’m 21, and I’ve actually known him for years; she even tried to set me up with him last summer. We flirted a little, nothing serious, but now he’s her boyfriend. It feels gross, like I’m part of some twisted fantasy. My mom has always been my best friend, the person I trusted most. This broke something in me. She knows how I feel about her dating guys close to my age, but younger than me? I can’t respect that. My young

Hey Uncle Gary, I got into a bit of a blowout with my mother-in-law after I asked my husband to run to the store and grab me some tampons last night. Personally, I didn’t think it was a big deal, and neither did he. For context: I’ve always had brutal cramps during the first few days of my period. We’re talking can’t-stand-up, curled-in-a-ball kind of pain. I was on birth control for over a decade to help manage it, but I recently stopped because my husband and I are trying t

Dear Uncle Gary, What do you say to someone who is dying at 33? Last November, my friend was diagnosed with an aggressive breast cancer. Now, less than a year later, she’s in palliative care. The doctors say she has “weeks.” Weeks. I’ve been crying for days, trying to make sense of something that refuses to make sense. She’s young. She’s vibrant. She’s supposed to be here. We've been friends since the first day of kindergarten. I want to visit her in the hospital, but I’m ter

Dear Uncle Gary, My husband told his family I was unfaithful, and now I feel exposed and ashamed. Can we rebuild trust after something like this, or do I need to accept that his loyalty to his family is greater than to us? Signed, The Cheater Dear “The Cheater, First, let’s strip away the label. You’re not a headline. You’re a human being who made a mistake, or maybe didn’t, depending on the full story, and now you’re standing in the wreckage wondering if anything can be rebu

Dear Uncle Gary, Last night, after my friend’s rehearsal dinner. I’m one of her bridesmaids, and everyone had left the restaurant except me and her fiancé. We stayed behind to help tie up a few loose ends. In the parking lot, he tried to kiss me. I pushed him away, and he laughed. Then he said, “The best part is, if you tell Sophia, she won’t believe you.” I’m stunned. I don’t know what to do. Should I tell her? Should I stay quiet and hope it never happens again? I feel sick

Dear Uncle Gary, I recently spent the day with a longtime friend I hadn’t seen in over a year. We attended university together, and he and his wife have just retired to Palm Springs, where I live. What was meant to be a pleasant reunion, golf, lunch, and drinks, quickly became uncomfortable. My friend has developed an off-putting habit: constant eye rubbing, nose picking, wiping mucus on his shirt, and picking at his ears. It continued throughout the day, on the green and at

Dear Uncle Gary, Our son is coming home from college, and he’s bringing someone he cares about, his boyfriend. We love our son deeply, but we’re struggling with how to handle this visit in a way that reflects both our Christian values and our desire to stay connected as a family. We’re unsure how to approach the conversation, especially around whether his boyfriend should stay in our home. How can we talk to our son honestly, without damaging our relationship? Signed, Good C

Dear Uncle Gary, I’ve just stepped into a national tour as the second hair supervisor, replacing someone who bailed for another gig. It’s been one week, and already I’m caught between two camps. Those who can’t stand the lead supervisor, and the few who swear by her. The show’s been on the road for six months, and not a single wig has been washed, despite Equity rules requiring weekly maintenance. The supervisor injured her hand on opening night and hasn’t been able to do her

Dear Uncle Gary, My adult child just came out as trans. I want to be supportive, but I’m terrified of saying the wrong thing. Where do I start? Signed, Confused Dad Dear Confused Dad, Let me start by saying this: your willingness to ask this question, to lean into the discomfort and uncertainty, is already a powerful act of love. You’re showing up. And that matters. Now, when your child comes to you with something as deeply personal as their identity, it’s not just a moment;

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 was a research scientist at a major pharmaceutical company until I got laid off. My wife is an attorney at a top law firm, and she’s doing very well. When the layoff happened, we talked it through and agreed I’d stay home with the kids for a while. It made sense at the time. She had the momentum, and I figured I’d take a breather, be the steady parent, and maybe even enjoy it. That was six months ago. Now I’m having second thoughts. I love my kids, but I mi

Dear Uncle Gary, I was laid off last month from my job as a university administrator. I didn’t tell my wife right away because I truly believed I’d find something quickly and then explain it once I had good news to soften the blow. But here we are, a month later, no interviews, no prospects, and I’m still pretending to go to work every morning. I feel ashamed, stuck, and scared. I know I need to tell her, but I don’t know how to begin. I’ve never lied to her like this before,

Dear Uncle Gary, I just started an amazing job as an assistant to a very successful hairstylist in Newport Beach. He’s super busy, well-known, and I was thrilled to be hired. About a month in, he asked me out. I froze. A few days earlier, he’d asked if I had a boyfriend, and I said no, I honestly thought he was gay, so I didn’t think anything of it. I panicked and said I like girls, mostly because I was afraid that saying no would cost me the job. Now I’ve heard he’s been ask

Dear Uncle Gary, I met my wife when I was 18, married her at 24, and we had our daughter at 25. Life felt full, with good careers, a happy kid, and what I thought was a strong marriage. But at 35, my wife told me she wasn’t happy. We divorced, stayed friends for our daughter’s sake, and a few years later, she remarried. Her new husband adopted our daughter with my blessing. Since the divorce, I’ve stayed single and started exploring my sexuality. I’d never been with men befor