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” is doing a lot of heavy lifting here. Is it betrayal because they snuck around? Lied? Or is it betrayal because they didn’t ask for your blessing, didn’t check in, didn’t even pause to consider how this might land with you? That matters. Intent matters. Timing matters. And history matters. Let’s talk about that history. Why did you and your ex break up? Was it messy, unresolved, full of lingering feelings? Or was it clean, mutual, and done? If your friend was around during the relationship listening to your complaints, watching the dynamic, then yeah, it’s fair to wonder; were they quietly auditioning while you were unraveling? That’s not just awkward. That’s a breach of emotional trust. But here’s the twist. Maybe they are a better match. Maybe they bring out something in each other that you never could. That doesn’t erase your discomfort, but it reframes it. It’s not about ownership. It’s about dignity. You don’t have to cheer them on, but you also don’t have to carry bitterness like a backpack full of bricks. So what do you do? You name the feeling. You sit with it. You ask yourself what you need to move forward, closure, distance, a conversation, or just time. And you remember this. Being “the bigger person” doesn’t mean swallowing your hurt. It means choosing how to respond with clarity and self-respect. You’re not petty. You’re processing. And that’s the work. Sincerely, Uncle Gary

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 faster. But here’s the nuance: staying doesn’t mean surrendering. It means strategizing. Use the paycheck as fuel, not a prison. Start laying the groundwork now, network, skill up, moonlight, and build your exit ramp brick by brick. The goal isn’t to escape, it’s to evolve. And don’t let the paycheck trick you into thinking you’re stuck. Money’s important, but so is meaning. You’re allowed to want both. You just have to be smart about the order in which you chase them. So yes, keep your ducks in a row. But make sure they’re marching toward something better. Because staying in a draining job forever isn’t noble, it’s just quiet resignation. And you deserve more than that. Best of luck, Uncle Gary

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 full job since, but management refuses to replace her. I’m trying to stay professional, but this feels like a sinking ship. Do I stick it out and finish the tour, or cut my losses before the wigs start crawling away? Signed, Second Supervisor Dear Second Supervisor, You didn’t just walk into a tour, you walked into a slow-motion train wreck with a wig closet full of biohazards and a supervisor who’s half idol, half liability. And now you’re expected to keep it professional while the ship lists hard to starboard. Let’s break this down. First, the wigs. Six months without a wash? That’s not just gross, it’s a violation. Equity rules aren’t optional, and if management’s ignoring them, they’re gambling with health, safety, and liability. You’re not just catching stray drama, you’re catching the fallout of a system that’s already broken. Second, the supervisor. She’s injured, she’s not performing her duties, and management won’t replace her. That’s not loyalty, it’s negligence. And it’s putting you in a position where your name, your reputation, and your sanity are on the line. So here’s the real question: Are you staying out of duty, or out of fear? If you believe you can make a difference, document the violations, advocate for proper hygiene, and protect the cast, then stay. But only if you’re backed by a union rep, a paper trail, and a spine of steel. If you’re being used as a Band-Aid on a bullet wound, walk away. You didn’t sign up to be the fall guy for someone else’s dysfunction. And leaving doesn’t make you a quitter; it makes you someone who knows their worth. Whatever you choose, don’t go quietly. Speak up. Protect yourself. And remember: you’re not just doing hair. You’re holding the line between professionalism and chaos. Signed, With admiration for your grit and a strong whiff of disinfectant, Uncle Gary

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; it’s a turning point. It’s a chance to affirm that your love isn’t conditional. That it doesn’t depend on expectations or assumptions. That it’s rooted in who they are, not who you thought they’d be. You’re afraid of saying the wrong thing. That’s human. That’s honest. But don’t let fear keep you silent. Start with humility. Say, “I may not have the right words yet, but I’m here. I love you. I’m listening.” That’s the foundation. From there, you build. And you don’t have to build alone. Family therapy can be a powerful space, not because something’s broken, but because you’re choosing to grow together. It’s a place to ask questions, to learn, to unlearn, and to strengthen the bond that brought you here in the first place. Support is always available. There are communities, counselors, resources, and people who’ve walked this path and want to help you walk it too. You don’t have to be perfect. You just have to be present. And here’s something else worth knowing. Trans people who identify and live outside their assigned gender at birth have existed throughout history, in every corner of the world. From the Two-Spirit people in Indigenous cultures, to hijras in South Asia, to fa’afafine in Samoa, gender diversity is not new. It’s not a trend. It’s part of the human story. Your child isn’t stepping outside tradition; they’re stepping into a legacy of authenticity, resilience, and truth. Support them in that journey. So start there. With love. With listening. With the courage to say, “Teach me.” Because when you do, you’re not just supporting your child, you’re honoring them. And that’s what family is all about. My Support is with you, Uncle Gary

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 “what could’ve been.” So here’s the deal. If you’re thinking of reaching out, ask yourself what you’re really hoping for. A clean apology? A second chance? A little relief from the guilt? Because if it’s closure, you can offer that. If it’s a disruption, if you’re hoping to shake something loose in their new relationship, then don’t. That’s not love, that’s your ego dressed up in nostalgia. But if you can own your silence, name your fear, and offer a simple truth, “I panicked, and I regret it,” without expecting anything in return, then maybe that message is worth sending. Not to reopen the door, but to close it with grace. And if you don’t reach out? That’s okay too. Sometimes the most honest thing you can do is sit with the discomfort, learn from it, and let it shape how you show up next time. No drama. No declarations. Just clarity. Best Uncle Gary

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 deserves respect. And it deserves clarity. Now, I know it’s tempting to soften the blow, to leave a little door cracked open. But that’s not kindness, it’s confusion dressed up in good intentions. If you care about this person, and it sounds like you do, then the most loving thing you can do is be clear. Not cruel. Not cold. Just clear. “You’re not auditioning for a rom-com, you’re starring in a very special episode of ‘Boundaries Are Beautiful!’ So go ahead, be honest, be gentle, and maybe throw in a hug or a weird dance move if it helps lighten the mood. But don’t let them build a castle on a cloud. You’re not the villain here. You’re the friend who chose truth over comfort. And that, my friend, is a beautiful kind of love. Sincerely Uncle Gary

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 muscle guy with a big...personality. The moment we walk into a room, it’s like watching a Marvel movie premiere, everyone’s lining up for a piece of Captain America, and I’m just holding the popcorn. The first few threesomes felt less like exploration and more like me watching Mike get worshipped while I sat there like a decorative throw pillow. But here’s the kicker: the moment someone shows interest in me, touches my arm, compliments my butt, Mike shuts it down like a jealous prom queen. Suddenly, he’s packing up, pouting, and ready to leave. Apparently, open relationships are only open when he’s the centerfold. So Uncle Gary, what do I do when my partner wants to share himself with the world but can’t handle anyone having a piece of me? Signed, Third Wheel in Throupleville Dear Third Wheel in Throupleville, You, my friend, have wandered into the wild west of modern romance, where the rules are flexible, the boundaries are blurry, and apparently, the spotlight is reserved for Mike and Mike alone. Let’s start here: you didn’t sign up to be a background dancer in someone else’s fantasy. You agreed to explore, not to disappear. And while open relationships can be thrilling, they only work when both partners are getting what they need, not just one guy getting his ego stroked while the other gets ghosted mid-threesome. Mike’s behavior isn’t just awkward, it’s telling. He’s fine being the main attraction, but the moment you get a little attention, he folds like a cheap beach chair. That’s not polyamory. That’s insecurity dressed up in a jockstrap. Now, I’m not here to shame anyone’s kinks or preferences. If threesomes aren’t your thing, that’s valid. If monogamy feels like home, don’t let anyone Airbnb your heart out of guilt. But if you’re going to keep exploring this open setup, you need a few things: Clear boundaries. What’s okay, what’s not, and what happens when someone crosses the line. Mutual respect. You’re not a prop. You’re a partner. Emotional honesty. If Mike’s ego can’t handle your desirability, that’s his homework, not yours. And if he keeps pouting every time someone finds you attractive? Maybe it’s time to close the relationship, not because open relationships don’t work, but because this one isn’t working for you . You deserve to be the star of your own story, not the understudy in someone else’s fantasy. Signed, Uncle Gary P.S. If Mike wants to be the only one getting attention, he can start a fan club. But in a relationship? You both deserve applause.

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 the front door of a house you’ve lived in for years. The door’s still yours. The memories behind it haven’t changed. But now it catches the light differently. It invites people in with a little more clarity. Here’s the trick: don’t confuse style with substance. Your values, kindness, grit, curiosity, whatever makes you you , those are the foundation. They’re the studs in the wall. What you’re updating is the wallpaper, the lighting, maybe the furniture arrangement. You’re not knocking the whole thing down. You’re just making it easier for people to see the real you when they walk in. And if you’re worried about losing yourself in the process, good. That means you care. That means you’re not chasing approval, you’re curating authenticity. Reinvention done right doesn’t feel like a costume change. It feels like finally wearing clothes that fit. So go ahead. Change your hair, your tone, your tagline. Just make sure it’s amplifying your truth, not muting it. The best version of you isn’t a departure, it’s a reveal. Signed, Uncle Gary P.S. If you ever feel like you’re faking it, pause and ask, “Is this me, just louder?” If the answer’s yes, you’re on the right track.

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 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

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