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 few arguments about where to eat. Coming out of that kind of bond isn’t just a breakup. It’s a full-body recalibration. So let’s start there: you’re not broken. You’re in transition. And transitions are messy, confusing, and often lonely. Now, about the body. You say you used to have a nice one. I’m going to bet you still do, maybe not the same one, but one that’s lived, one that’s earned its stories. And if you’re still good-looking (your words, not mine), then let’s not bury the lead. You’ve got something to work with. As for going out and not meeting anyone? That’s not a failure. That’s data. You’re showing up. You’re trying. You’re noticing. And yes, the crowd might skew young, but that doesn’t mean you’re invisible. It just means you’re in the wrong room for the kind of connection you’re craving. So where do you start? You start by remembering that you’re not auditioning. You’re not trying to be twenty-five again. You’re trying to be fifty-five with grace, humor, and maybe a little flirt left in the tank. You start by finding spaces that feel like you , not like the version of you your friends are chasing. That might mean skipping the loud bar and trying a gallery opening, a queer book club, a volunteer gig, or even a dating app that lets you filter for grown-ups. And while you’re at it, be kind to your body. Feed it well. Move it in ways that feel good. Dress it in something that makes you stand a little taller. Not because you need to impress anyone, but because it reminds you that you’re still here, still worthy, still very much in the game. Loneliness isn’t a permanent state. It’s a signal. It’s your heart saying, “I’m ready for something new.” And that’s not sad. That’s brave. Best Regards, Uncle Gary

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 before, but I’ve grown more comfortable with that part of myself, even though I’m not officially out. I travel a lot for work and meet people when I’m out of town. One of them is Mike, he’s 26, I’m 38, and we’ve been seeing each other when I’m in California. I haven’t told him everything about my life, and I’ve kept him separate from my world in Chicago. Then came the twist. My daughter recently got married, and at the rehearsal dinner, Mike walked in. Turns out, he’s my daughter’s fiancé’s brother. We were both shocked. When my daughter and her new husband asked how we knew each other, I lied. Mike followed my lead and lied too. Now it’s a month later, and I’m sitting with the fallout, the secrecy, the awkwardness, the missed chance to be honest. Signed, What do I do now? Dear What Do I Do Now, Well. That’s a plot twist worthy of a standing ovation and a stiff drink. You walk into your daughter’s rehearsal dinner expecting chicken or fish, and instead, you get Mike, the man you’ve been quietly seeing in California, is standing there like the universe just threw a pie in your face. Let’s take a breath. You didn’t do anything unforgivable. You did what most people do when they’re caught off guard: you reached for the nearest exit. In this case, it was a lie. Not ideal, but understandable. You weren’t ready. You hadn’t told Mike everything. You hadn’t told your daughter anything. And suddenly, your two worlds collided in a room full of white linen and family expectations. Now you’re sitting in the aftermath, wondering how to clean it up. Good news: you can. But it’s going to take a little courage and a lot of clarity. Start with Mike. He deserves a conversation that’s honest, not dramatic. Something like, “I didn’t expect our lives to intersect like that. I panicked. I wasn’t ready to explain everything, and I’m sorry I put you in that position.” That’s not a weakness. That’s respect. Then, if your daughter or her husband brings it up again, and they probably will, you don’t need to give them a full autobiography. You just need to own the moment. “Mike and I met while I was traveling. We got to know each other. I didn’t realize he was part of the family until that night, and I wasn’t sure how to handle it.” That’s enough. That’s honest. That’s adult. Now, let’s talk about the bigger picture. You’ve been exploring your sexuality quietly, privately, and with care. That’s brave. You don’t owe anyone a label. You don’t owe anyone a coming-out party. But you do owe yourself the freedom to stop treating your truth like a liability. You’re 38. You’ve lived. You’ve raised a daughter. You’ve built a life. And now you’re discovering a part of yourself that was waiting patiently in the wings. That’s not something to hide. That’s something to honor. So what do you do now? You stop lying. You start talking. You give Mike a little grace. You give yourself a little credit. And you remember that the people who matter will care more about how you treat them than who you’re dating. And if anyone gives you grief, just smile and say, “Life’s full of surprises. I’m one of them.” Oh, and please consider going to therapy. It doesn’t mean you’re weak or crazy. It’s just what smart adults do when they need a little clarity. Best Regards, Uncle Gary

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 asking clients if they knew I like girls, and I feel like I’ve created a mess I don’t know how to clean up. What should I do? Signed, Mess-Maker Dear Mess-Maker (and I say that with love), First, congratulations on landing the job. Newport Beach, high-profile stylist, fresh start, that’s no small thing. You earned it. Now, about the deer-in-headlights moment. You were caught off guard, and you did what a lot of people do when they feel cornered: you said something to deflect, to protect, to buy time. That doesn’t make you dishonest. It makes you human. But now the moment has passed, and the story you told is walking around the salon without you. That’s the part we need to fix. Here’s the truth: your boss crossed a line. Asking if you have a boyfriend is one thing. Asking you out when you’re brand new and working under him? That’s a power imbalance. And now he’s chatting with clients about your sexuality like it’s salon gossip. That’s not just inappropriate, it’s unprofessional. You don’t owe him a romantic explanation. You don’t owe him a label. What you do owe is yourself a little clarity and a lot of self-respect. If you feel safe doing so, pull him aside and say, “I want to be clear, I’m here to work. I’m grateful for the opportunity, but I’m not comfortable with personal questions or conversations about my private life being shared with clients.” You don’t have to explain the panic. You don’t have to revisit the lie. You just have to reset the boundary. And if that feels too risky, document what’s happening. Keep notes. Talk to someone you trust. Because if this escalates or affects your job, you’ll want a record. You’re not the problem here. You’re the professional trying to navigate a tricky situation with grace. And that’s something to be proud of. Best Regards, Uncle Gary

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 jawline. A good jaw can make you overlook a lot, questionable playlists, suspicious cologne choices, even the occasional “I love The Big Bang Theory” confession. But clapping when the plane lands? That’s a bold move. That’s a man who treats Delta like dinner theater. Now, is it a red flag? Not necessarily. It’s not like he’s booing the pilot or trying to start a wave. He’s just... enthusiastic. And maybe a little performative. But let’s be honest, we’ve all got quirks. Some people hum while they eat. Some people say “anywho” unironically. Some people still wear cargo shorts. The real question is: does this bother you because it’s embarrassing, or because it feels like a mismatch in how you both move through the world? If you’re someone who values quiet dignity and he’s out here giving standing ovations to basic transportation, that’s worth noticing. But if it’s just a moment of cringe in an otherwise lovely relationship, maybe let it go. Or better yet, lean in. Next time he claps, whisper, “Encore!” and see if he gets the joke. Because love isn’t about finding someone who never claps. It’s about finding someone whose clapping doesn’t make you want to fake a medical emergency. Best Regards, Uncle Gary

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 Wheel with a Smile, You are not wrong for feeling what you feel. You are not bitter. You are not broken. You are human. Your best friend is stepping into a new chapter, and you are standing on the sidelines with a smile that is starting to feel heavy. That does not make you a bad friend. That makes you honest. You are allowed to celebrate her joy and still feel the sting of your own longing. You are allowed to cheer for her and still wonder when someone will cheer for you. That ache is not jealousy. It is hope that has not found its match yet. So how do you show up without losing yourself in the process You stay present. You stay kind. You let yourself feel the full range of emotions without shame. You do not have to fake enthusiasm. You do not have to pretend you are fine. You just have to be real. And when someone asks why you are still single, you can smile and say, I am waiting for someone who sees me the way I see myself. You are not behind. You are not less than. You are simply in your own season. And it is still unfolding. Best Regards, Uncle Gary

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 apps, and they make me feel like I’m auditioning for a role I don’t even want. I don’t need a husband. I don’t need a cruise partner. I just want to feel close to someone again. Is that foolish at my age? Signed, Still Got Skin in the Game Dear Still Got Skin in the Game, You are not foolish. You are not past your prime. You are not asking for too much. You are asking for something deeply human. To be touched, to be seen, to be wanted. And if anyone tries to tell you that desire has an expiration date, you can smile politely and then ignore them with the full force of your wisdom. You’ve lived. You’ve raised children. You’ve built a life. And now you’re sitting in the quiet, wondering if there’s still room for closeness. Not just sex, though, let’s not pretend that’s off the table, but the kind of intimacy that comes from being known. Dating apps are not built for nuance. They’re built for swiping and slogans. You are not a slogan. You are a story. And you deserve to be met with curiosity, not algorithms. So, where do you go? You go where grown men go when they’re not trying to impress anyone. You go to the places where people linger. Try your local library’s author talks or lecture series. Not the ones about cryptocurrency or startup culture, but the ones about memoir, history, or gardening. Look into community college continuing ed classes. Not because you need to learn anything, but because the guy sitting next to you might be there for the same reason. Check out local volunteer groups that attract people with time and heart. Food banks, historical societies, and even city beautification projects. You’ll find men who show up, who care, and who are not afraid to get their hands dirty. If you like music, go to the jazz nights, the acoustic sets, the outdoor concerts where people bring folding chairs and wine in plastic cups. That crowd knows how to relax. And if you’re feeling bold, walk into a senior center and ask about their social calendar. You might be surprised. Some of those folks are dancing twice a week and dating like it’s 1975. You are not looking for fireworks. You are looking for a slow burn. The kind of connection that feels like a warm blanket, not a performance. So go where the warmth is. Go where the grown-ups are. And go as yourself, not auditioning, not shrinking, not pretending. Because you still have skin in the game. And that skin deserves to be held. Best Regards, Uncle Gary

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, and I’m afraid this will break something between us. How do I come clean without losing her trust? Signed, Out of Work and Out of Words Dear Out of Work and Out of Words, Let me start with the obvious: you’re not the first person to get laid off, and you sure won’t be the last. But the part that’s eating at you isn’t the job loss, it’s the silence. It’s the mornings spent pretending, the afternoons spent refreshing job boards, and the nights spent rehearsing the conversation you still haven’t had. You didn’t lie because you’re cruel. You lied because you were scared. You wanted to protect your wife, protect your pride, protect the illusion that everything was still under control. That’s not evil. That’s human. But here’s the thing. Silence has a shelf life. And yours is starting to smell. You need to tell her. Not because you’re ready, but because it’s time. Because every day you wait, the truth gets heavier and the trust gets thinner. And the longer you carry this alone, the harder it’ll be to put it down. So how do you do it? You sit her down. You take a breath. And you say something like this: “I need to tell you something I should’ve said a month ago. I lost my job. I didn’t want to worry you. I thought I’d fix it before you had to know. But I haven’t. And I’m sorry.” Then you stop talking. You let her react. You let her feel whatever she needs to feel. And you stay in the room. Because this isn’t just about employment. It’s about partnership. It’s about showing her that when things fall apart, you don’t disappear. You show up. Now, she might be upset. She might be hurt. She might ask why you didn’t trust her with the truth. And you’ll have to answer that. Not with excuses, but with honesty. “I was ashamed. I didn’t want to disappoint you. I thought I could fix it before it became a problem.” That’s not a weakness. That’s accountability. And here’s the part you need to remember. You’re not just telling her you lost a job. You’re telling her you’re ready to stop hiding. That’s the beginning of the repair. That’s the beginning of real intimacy. You’re still in the game. You’re still capable. You’re still worthy of love, respect, and a damn good comeback story. So go tell her. Not because you have a solution. But because you finally have the courage to be seen. Best Regards, Uncle Gary

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 miss the lab. I miss the work. I miss the part of me that felt sharp and useful and caffeinated by something other than Paw Patrol. I feel like I’ve traded my identity for a never-ending loop of laundry, snacks, and trying to explain why glitter is not a food group. My wife is thriving. She’s supportive, but she’s also exhausted. I don’t want to add pressure by saying I want to go back to work when we built this plan together. But I also don’t want to keep pretending I’m fulfilled when I’m quietly unraveling. How do I bring this up without sounding ungrateful or like I’m trying to bail on our family? Signed, Dad in a Lab Coat (and Yoga Pants) Dear Dad in a Lab Coat (and Yoga Pants), You are not failing. You are not flaking. You are not the first person to wake up six months into a “great idea” and realize it feels more like a hostage situation with juice boxes. You made a thoughtful decision. You and your wife looked at the layoff, looked at the kids, looked at the calendar, and said, “Let’s try this.” That’s not a weakness. That’s strategy. That’s partnership. That’s two grown adults trying to make life work without a manual. But now you’re in it. And it turns out, being the stay-at-home parent is not just snack prep and story time. It’s identity erosion in slow motion. It’s wondering if your brain still works while you’re scraping dried Play-Doh off the dog. You miss the lab. You miss the part of yourself that felt sharp and curious and caffeinated by something other than lukewarm coffee and existential dread. That’s not selfish. That’s self-awareness. So here’s what you do. You tell your wife. Not with guilt. Not with a PowerPoint. Just with honesty. “I’ve been thinking. I’m grateful for this time with the kids, but I’m starting to feel like I’ve lost a part of myself. I miss the work. I miss the rhythm. I want to start looking again. And I think it’s time we look into hiring a nanny.” Then you stop talking. You let her respond. You let her feel whatever she feels. And you stay in the room. Because this isn’t about abandoning your family. It’s about reclaiming your balance. You’re not asking to be rescued. You’re asking to be restored. And if she’s the partner you’ve described, smart, successful, supportive, she’ll hear you. She might not have the solution. But she’ll respect the honesty. Now, will it be easy? No. You’ll have to juggle. You’ll have to compromise. You’ll have to figure out how to chase your career without dropping the kids or your sanity. But you’ve done harder things. You’ve worked in pharmaceuticals. You’ve survived glitter. You can do this. So go have the conversation. Not because you’re desperate. But because you’re ready. And if anyone tries to tell you that dads should just “man up and stay home,” feel free to smile and say, “I did. Now I’m manning up and moving forward.” Best Regards, Uncle Gary

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 same time. And I’m over here Googling “how to roast a chicken for one” and pretending I’m fine. Is it possible to want more without knowing exactly what “more” means? Signed, Good on Paper, Weird in the Heart Dear Good on Paper, Weird in the Heart, Let’s skip the polite nodding and get straight to it. You’re not broken. You’re not lost. You’re just waking up to the fact that a life built on checkboxes doesn’t always check out. You’ve got the job, the apartment, the dog who thinks you’re a Nobel laureate every time you open the treat jar. You’ve got friends who show up and a calendar that looks full enough to impress your dentist. But somewhere in all that structure, something’s gone quiet. That quiet isn’t failure. It’s a signal. It’s your soul tapping you on the shoulder and whispering, “Hey, remember me?” Now, you don’t need to blow up your life. You don’t need to move to Bali or start a podcast about artisanal toast. You just need to listen. And one of the best ways to really listen is to talk to someone who knows how to ask the right questions. Therapy isn’t a last resort. It’s a front-row seat to your own mind. It’s where you get to say, “I don’t know what I want,” and have someone reply, “Let’s find out.” You don’t have to be in crisis to deserve clarity. You just have to be curious. So go find a therapist who doesn’t blink when you say, “My life looks great but feels weird.” Someone who can help you unpack the difference between comfort and fulfillment. Between being fine and being alive. And if anyone tries to tell you therapy is for people who can’t handle life, feel free to smile and say, “Exactly. I’m done handling. I’m ready to understand.” You’re not asking for too much. You’re asking for something real. Best Regards, 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 generic printed text. I assumed it was something from Amazon. But when I opened it, I was stunned. Inside were two pairs of used men’s underwear. And they weren’t my husband’s. They were stiff, smelled awful, and looked like something no one should ever touch, let alone mail. My first thought was that maybe some woman mailed them back to him, but I checked, and he doesn’t own anything like them. Now I’m spiraling. Did he buy them? Is someone playing a sick joke? Is this some bizarre fetish thing I don’t know about? I don’t know how to ask him without sounding accusatory or like I’ve lost my mind. But I also can’t pretend this didn’t happen. What do I do? Signed, Postpartum and Panicking Dear Postpartum and Panicking, First, let me say, I hear you. I hear the confusion, the fear, the exhaustion, and the ache for clarity in a moment that feels anything but clear. You’ve been through a lot. You’re five months postpartum, navigating the physical and emotional terrain that comes with bringing new life into the world. That alone is a full-time job. And now, on top of that, you’re holding a mystery in your hands that feels unsettling, even surreal. Let’s start with the facts. A package arrived. No return address. Generic envelope. Inside, two pairs of used men’s underwear that don’t belong to your husband. That’s not just strange, it’s alarming! And it’s okay to feel freaked out. Now, when something this bizarre shows up in your life, your mind starts racing. Is this a prank Is it something darker? Is it connected to your husband in a way you don’t understand Here’s what I want you to remember: you don’t have to solve this alone. You don’t have to carry the weight of this mystery in silence. And you certainly don’t have to pretend everything’s fine when your instincts are telling you otherwise. So yes, you ask him. Not with accusation. Not with anger. But with honesty. “Hey, something strange came in the mail today. I need to talk to you about it.” You show him the package. You describe what you found. And then you listen. You give him space to respond. Because if there’s an explanation, whether it’s a prank, a mistake, or something more complicated. You deserve to hear it directly. And if there isn’t an explanation, if the response is evasive or dismissive, then you have more information. Not about the underwear, necessarily, but about the state of your communication. About the trust between you. Now, let’s talk about the deeper layer. You mentioned intimacy has been scarce. That you’re the one initiating. That you’re carrying the weight of postpartum recovery, emotional vulnerability, and now this strange event. That’s a lot. And it’s okay to say, “I need help.” This might be a moment to consider couples therapy. Not because something’s broken, but because something’s unclear. Therapy isn’t a punishment. It’s a tool. It’s a place where you can say, “I’m confused,” and have someone help you sort through the noise. You deserve clarity. You deserve respect. You deserve to feel safe in your own home. So take a breath. Trust your instincts. And start the conversation. You’re not crazy. You’re not overreacting. You’re a woman standing in the middle of a strange moment, asking for truth. And that’s brave. With respect, 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, 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