Dear Uncle Gary, I caught my teenager lying about something small. Do I let it slide, or is this the moment to make it a big deal? Signed Concerned Dad Dear Concerned Dad, You’re right to say something. Not because the lie was catastrophic, but because silence teaches just as loudly as words do. If you let it slide, you’re not just ignoring the fib; you’re unintentionally signaling that truth is negotiable when the stakes are low. And that’s a dangerous seed to plant. Small l

Dear Uncle Gary I’m 42, single, and child-free by choice, but my family keeps treating me like I’m unfinished. How do I shut that down without burning bridges? Signed, 42 and single Dear 42 and Single, You’re not unfinished. You’re not waiting to be picked. You’re not a puzzle missing the “spouse and kids” corner piece. You’re a whole damn mural, and if your family can’t see that, it’s not because you’re incomplete. It’s because they’re looking through a lens that doesn’t fit

Dear Uncle Gary, My best friend just started dating my ex. They say it’s love, but I feel betrayed. Am I being petty, or do I have a right to be upset? Signed Betrayed Dear Betrayed, You’re not being petty. You’re being human. When someone close to you crosses into territory that used to be yours, especially emotionally intimate territory, it stirs things up. That doesn’t mean you’re wrong to feel what you feel. It means you’re alive. Now, let’s zoom out. The word “betrayed”

Dear Uncle Gary, I’m stuck in a job that pays well but drains my soul. Is it reckless to walk away without a backup plan? Signed, Reckless Dear Reckless, You're absolutely right, it’s not just reckless, it’s potentially self-sabotaging. In this economy, walking away without a plan isn’t a bold leap; it’s a blindfolded dive into shallow water. The job market’s unpredictable, and while soul-draining work can feel like a slow death, financial instability can hit harder and faste

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, I ghosted someone I genuinely liked because I panicked. Now they’re dating someone else, and I feel sick. Do I reach out or let it go? Signed, Kicking Myself Dear Kicking Myself, You ghosted someone you genuinely liked. Not because you didn’t care, but because something in you hit the panic button. That’s not a crime, it’s a moment. But moments have consequences, and now they’re with someone else. And you’re stuck in that aching space between “what was” and “

Dear UncleGary, My best friend just confessed they’re in love with me. I love them too, but not like that. Do I tell the truth or let them believe there’s hope? Signed, Not Feeling it Dear Not Feeling It, First off, this is one of those moments that calls for courage. Not the loud kind, but the quiet kind, the kind that shows up when you look someone you care about in the eye and tell the truth, even when it’s uncomfortable. Because love, in any form, deserves honesty. It des

Dear Uncle Gary, How do I change my image without losing myself? Signed Evolving in Evansville Dear Evolving in Evansville, First off, I love the question. It’s brave, it’s honest, and it’s something most people wrestle with quietly while pretending they’ve got it all figured out. So let’s crack it open. Changing your image isn’t about swapping out your soul for something trendier. It’s about alignment, making sure the outside matches the inside. Think of it like repainting t

Dear Uncle Gary, How do I say no to friends trying to sell me things? Signed, Pitched in Portland Dear Pitched in Portland, Say no once, clearly. “I value our friendship, but I’m not interested.” If they keep pushing, they’re choosing the sale over the relationship. That’s not on you. That’s just good information. Signed, Uncle Gary

Uncle Gary, How do I know if my goals are realistic? Signed, Dreamer in Duluth Dear Dreamer in Duluth, If they scare you but don’t paralyze you, they’re perfect. The right goal should make your stomach flip a little. It should whisper, “This might be too big,” while your gut replies, “Let’s try anyway.” If you’re frozen, it’s too much. If you’re bored, it’s too little. But if you’re nervous and moving forward, that’s the sweet spot. Signed, Uncle Gary

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 38, single, and I’ve built a life that looks pretty good on paper. I’ve got a solid job, a decent apartment, a dog who thinks I’m a superhero, and friends who show up when it counts. But lately, I’ve been feeling this quiet panic, like I missed something. I never really wanted the white-picket-fence life, but now I’m wondering if I skipped too many chapters. I see people settling down, having kids, building routines that look boring and beautiful at the s

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’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 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

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