Your Trusted Advisor.  "Wise men don't need advice; Fools won't take it" -Benjamin Franklin

Dear Uncle Gary, How do I rebuild trust with someone who says they forgive me, but still keeps their distance? Signed, Trying Dear Trying, Forgiveness is a door. Trust is the long walk back through it. When someone says they forgive you but still keeps their distance, it doesn’t mean they’re lying. It means they’re healing. Forgiveness is a gift they gave you. Trust is a gift you’ll have to earn. So here’s what you do, you show up. Not with grand gestures or guilt-soaked apologies, but with consistency. With patience. With proof, not just that you’re sorry, but that you’ve changed. That you understand what hurt them, and you’re not asking them to hurry past it. Let them set the pace. Let them have space. And when they peek out to see if it’s safe, let them find you being kind, being honest, being steady. You don’t rebuild trust by asking for it. You rebuild it by becoming someone who deserves it. And if they never fully come back? You still get to become that person. With hope and humility, Uncle Gary

Dear Uncle Gary, I just turned 40 and still don’t know what I want to be when I grow up. Is that normal, or am I just lost? Signed, Peter Pan Dear Peter Pan, First off, welcome to the club. Membership includes artists, accountants, baristas, and I know at least three retired dentists who still don’t know what they want to be when they grow up. You're not lost. You're just alive. Forty isn’t a deadline. It’s a checkpoint. I totally changed my life at forty. I’m in the process of changing things at sixty-five. And if you’re asking the question, that means you’re still curious, still searching, still open. That’s not failure. That’s fuel. The myth is that grown-ups have it all figured out. The truth is, most of us are winging it with a mix of hope, habit, and caffeine. Some people find their calling at 22. Others stumble into it at 63 while trying to fix a broken toaster and realizing they love working with their hands. So what now? Start small. Follow the itch, not the map. What makes you lose track of time? What do people thank you for? What would you do even if it didn’t pay? That’s the trailhead. And remember: Peter Pan never grew up, but he sure knew how to fly. Love, Uncle Gary P.S. If you ever want to talk about what lights you up, or what scares you, I’m here.

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 rebuilt. That takes guts. Here’s the hard truth: trust isn’t just about fidelity. It’s about how we handle each other’s pain. Your husband didn’t just share a private wound, he handed it to people who weren’t equipped to hold it gently. That’s not loyalty. That’s deflection. So yes, rebuilding is possible. But only if both of you are willing to do the messy, unglamorous work of repair. That means honesty, boundaries, and a shared commitment to protect the relationship from outside interference. If he’s more concerned with his family’s opinion than your healing, that’s not partnership, it’s performance. Ask yourself: is he angry, or is he cruel? Is he hurt, or is he punishing you? There’s a difference. And it matters. You’re allowed to want forgiveness. You’re allowed to want privacy. And you’re allowed to ask for a love that defends you, even when you’ve stumbled. You’re also allowed to ask his participation in couples therapy. You both need a little help right about now. Love, Uncle Gary P.S. Shame thrives in silence.

Dear Uncle Gary, My dad keeps forwarding me articles about ‘the dangers of oat milk.’ Should I be worried, or just block him? Signed Milk Man Dear Milk Man, Look, your dad’s oat milk crusade isn’t really about oat milk. It’s about connection. It’s about trying to stay relevant in your life, even if the method is… well, alarmist dairy propaganda. So before you block him, maybe ask yourself: when’s the last time you two actually talked? Not texted. Not exchanged articles. Talked. Because sometimes people send links when they don’t know how to say, “I miss you,” or “I’m not sure where I fit in your world anymore.” You don’t have to agree with him. You don’t even have to read the articles. But maybe you pick up the phone. Say, “Hey Dad, I got your oat milk thing. You doing okay?” And let the conversation go where it needs to. Worst case, you get a lecture on emulsifiers. Best case, you get your dad back. Best, Uncle Gary

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 just thinking about it. Sincerely, Caught in the Worst Kind of Secret Dear Caught in the Worst Kind of Secret, You’re in a painful spot, and I want to start by saying: I believe you. That moment in the parking lot wasn’t just inappropriate; it was calculated. That line he threw at you? “She won’t believe you.” That wasn’t a joke. That was a power play. He’s banking on silence. He’s betting on your fear. And he’s hoping shame will do the rest. Now, let’s be honest. If you tell Sophia, there’s a chance she won’t believe you. Not because you’re untrustworthy, but because denial is easier than heartbreak. She’s on the edge of a life she’s been planning, and the truth you carry could shatter it. That’s a heavy truth to hold. But here’s the deeper truth: silence protects no one but him. If you say nothing, he walks into that marriage with a secret and a smirk. If you speak up, you give Sophia the dignity of choice. You give her the chance to ask questions, to confront, to decide for herself what kind of man she’s marrying. You don’t have to make it dramatic. You don’t have to make it public. But you do have to decide what kind of friend you want to be, and what kind of peace you want to live with. Because this isn’t just about one kiss. It’s about whether you let someone use your silence to rewrite the truth. And if he ever tries that line again, “She won’t believe you”, you can look him dead in the eye and say, “That’s not your call to make.” With strength and grace, Uncle Gary

Dear Uncle Gary, Is it weird that I enjoy eating dinner alone more than with friends? Signed, Recluse Dear Recluse, Not weird. Not even close. In fact, I’d argue it’s a sign of emotional maturity, and possibly excellent taste in dinner companions. There’s a quiet kind of magic in solo meals. You get to eat what you want, when you want, without negotiating over appetizers or pretending you’re fascinated by someone’s latest juice cleanse. You can savor the silence, binge a show, read a book, or if you’re at a restaurant, you can just look into the crowd of people in the place like a philosopher with a fork. Now, if you’re only eating alone because the idea of company makes you break out in hives, that’s worth exploring. But if it’s simply your preferred vibe, your way of recharging, reflecting, or just enjoying your own damn company, then lean in. The world’s loud enough. Dinner doesn’t have to be. Besides, some of the best conversations happen when no one’s talking. Love, Uncle Gary P.S. If you ever want to invite someone to dinner who won’t interrupt your chewing with unsolicited life advice, I know a guy.

Dear Uncle Gary, I’m a sophomore at my dream university in Rhode Island, and I just pledged my dad’s old fraternity. He’s white, my mom’s Black, and growing up, I heard all his stories of brotherhood, campus life, the whole legacy, and I was excited to build my own version of that. So far, everyone’s been welcoming. But now and then, I hear things like, “You’re not like those other guys,” or “I think of you as one of us.” It’s subtle, but it stings. I know they mean it as a compliment, but it’s laced with assumptions about race that they don’t even realize they’re making. I don’t want to be the guy who’s always calling things out. But I also don’t want to keep swallowing these comments like they’re harmless. How do I speak up without being labeled as overly sensitive? Signed, One of Us Dear One of Us, Those comments, “You’re not like those other guys,” “I think of you as one of us,” aren’t compliments. They’re coded. They’re casual racism dressed up as inclusion. And they’re exhausting. You’re navigating a legacy system built for someone else, wearing a smile while people try to decide if you “count.” Your dad’s fraternity may have opened the door, but you’re the one walking through it with a different history, a different lens, and a whole lot more to carry. So how do you speak up without being labeled hypersensitive? You start by trusting your gut. If it bugs you, it matters. You don’t have to launch a TED Talk every time someone says something off. Sometimes it’s as simple as: “Hey, I know you didn’t mean anything by that, but it lands weird.” Or: “That kind of comment makes me feel like I’m being measured against a stereotype.” You’re not calling anyone a racist. You’re calling attention to a blind spot. And if they care about you, they’ll listen. If they don’t, well, that tells you something, too. You’re not there to educate everyone. But you are allowed to protect your peace. You’re allowed to say, “That’s not okay,” and still be part of the brotherhood. Because real brotherhood doesn’t ask you to shrink yourself to fit in. It makes room. Keep showing up. Keep speaking up. And remember: you’re not the problem. You’re the upgrade. With respect and a raised eyebrow, Uncle Gary

Dear Uncle Gary, I’m 28, confident, successful, and, if I may say so, easy on the eyes. I’ve developed a serious crush on my dentist. He’s gorgeous. Movie-star smile, strong hands, the kind of presence that makes you forget your mouth is full of cotton. I don’t know if he’s gay. His online footprint is all business degrees, credentials, and office hours. No personal clues, no social media breadcrumbs. But when I’m in the chair, I swear there’s something. He leans in close, sometimes resting his crotch against my hand or shoulder. I never move. I just let myself enjoy the warmth, the proximity, the possibility. But he never reacts. No wink, no shift, no signal. It’s like he doesn’t even notice. Am I imagining this? Or is there a chance he feels it too? Should I take the risk and ask him out, or keep my fantasies confined to the dental chair? Sincerely, Confused and a little turned on Patient Dear Confused and a little turned on Patient, I’ve had root canals with less tension than what you’re describing. Let’s start with the obvious: you’re not the first person to fall for someone who flosses professionally. But before you start planning your wedding registry at Harrods and Bergdorf Goodman, let’s take a breath. Now, I don’t know if your dentist is gay, straight, or just really committed to ergonomics. That little lean-in you’re describing? Could be accidental. Could be intentional. Could be an OSHA violation. But unless he’s whispering sweet nothings between rinses, I wouldn’t read too much into it. Here’s the thing: you’re charming, you’re confident, and you’ve got a pulse, which already puts you ahead of most people in the waiting room. But this is a professional setting. If you ask him out and he’s not interested, or worse, feels uncomfortable, you risk turning your next cleaning into a very awkward silence. So what do you do? You wait. You look for a sign outside the dental chair. A smile that lingers. A conversation that goes beyond fluoride. If you get nothing, you let it go. Because the only thing worse than unrequited love is being ghosted by someone who still holds your molars in their hands. And if it turns out he is interested? Well, then you’ve got yourself a love story with great dental coverage. With admiration and a raised eyebrow, Uncle Gary

Dear Uncle Gary, How do I stop doomscrolling without feeling like I’m missing the end of the world? Signed, Worried Scroller Dear Worried Scroller, First, let me assure you, if the world ends, someone will text you. Probably your cousin. Possibly in all caps. Now, about that doomscrolling. You’re not alone. The internet is a buffet of anxiety, and your brain keeps going back for seconds because it thinks it’s being helpful. “If I just read one more article, I’ll be prepared.” Prepared for what? A meteor strike? A congressional hearing? A raccoon uprising? Here’s the trick: swap “staying informed” with “staying sane.” You don’t need to know everything the moment it happens. You need to know enough to be a decent citizen and a kind human. That’s it. The rest is noise dressed as urgency. Try this: set a timer. Give yourself 15 minutes a day to check the news. Not 15 minutes per app, per rabbit hole, per existential spiral. Just 15. Then close the tab and open your life. Call a friend. Water a plant. Read something that doesn’t involve the phrase “unprecedented times.” And if you’re still worried, you’ll miss the end of the world? Don’t. It’ll trend. With love and a well-curated feed, Uncle Gary

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 the clubhouse. I was so unsettled by his behavior that I canceled our evening plans with our wives. I’m unsure how to address this without causing embarrassment or damaging the friendship. What would you do? Sincerely, Grossed Out Dear Grossed Out, You did the right thing. There’s no rule that says friendship requires enduring a full-body hygiene meltdown over lunch. Still, this is tricky. You care about this person. You have history. But now you’re faced with a behavior that’s not just unpleasant, it’s disruptive. And the worst part? He may not even realize it. If you want to preserve the friendship, you’ll need to decide whether to speak up or step back. A gentle, private conversation might help, something like, “I noticed a few habits that made me uncomfortable. I value our time together, but I wasn’t sure how to bring it up.” It’s awkward, yes. But it’s also honest. If that feels impossible, you’re allowed to create distance. Not out of judgment, but out of self-respect. You’re not obligated to endure discomfort just because someone used to be less gross. Friendship in retirement should feel like a reward, not a test of your gag reflex. With sympathy and sanitizer, Uncle Gary

Dear Uncle Gary, My boyfriend Jake and I have been together for almost six months. We’re both in our early 20s, still living at home, me juggling community college and a part-time job, him working full-time as a mechanic. Lately, something’s shifted. He’s distant. I still drop by after school, but when he’s home, he barely looks up from his phone. We talk, but he never wants to hang out. I figured maybe he was over it, and I started preparing myself to move on. Then his mom called, asking why I hadn’t been around. I told her Jake doesn’t seem interested anymore. She sounded surprised. Now I’m wondering: is he pulling away, or just disappearing into his screen? It feels like I’m competing with a phone, not another woman. I don’t know how to reach him anymore, and I’m not sure if I should keep trying. What do you do when someone fades out but never says goodbye? Signed, What Happened to Jake Dear What Happened to Jake, Something shifted, and you felt it before anyone said a word. That’s the thing about emotional distance, it doesn’t slam the door, it just slowly stops answering it. Jake’s behavior sounds like a slow fade, not a clean break. He’s present but not engaged, polite but not connected. And while his mom’s call might suggest he hasn’t told her much, it doesn’t change the fact that you’re being left to guess. That’s not fair, and it’s not love. Now, about the phone. It’s easy to blame the screen, it’s always on, always responsive, never asks for emotional vulnerability. But the real issue isn’t the phone. It’s that Jake’s using it to hide. From you, from himself, maybe from whatever feelings he doesn’t know how to deal with. You deserve someone who shows up with both presence and intention. Someone who doesn’t make you feel like you’re interrupting their scroll. If Jake can’t offer that, and won’t talk about why, then yes, it’s okay to walk away. Not out of anger, but out of self-respect. And if he ever wonders why you stopped showing up, you can say: “I didn’t disappear. I just stopped chasing silence.” With love and clarity, Uncle Gary

Dear Uncle Gary, I’ve been dating someone wonderful for about six months. We laugh a lot, the chemistry’s great, and I’m genuinely crazy about her. Lately, I’ve been wanting to go deeper, share more of myself, and learn more about her. But whenever I ask about her family or her past, she either changes the subject or says she doesn’t want to talk about it. At first, I chalked it up to privacy or timing, but it’s starting to feel... off. I even tried looking her up online. Nothing came up. No social footprint, no breadcrumbs. I don’t want to be pushy, but I also don’t want to ignore my gut. Should I press for answers, or give her more time and space? Signed, Curious but Cautious Dear Curious but Cautious, You’re not wrong to feel the tension between patience and curiosity. Six months in, it’s natural to want more than just good vibes, you want depth, history, context. You’re building something real, and real things need roots. Now, her reluctance could mean a few things. Maybe she’s been hurt. Maybe her past is complicated, or painful, or just not something she’s ready to share. That’s valid. But so is your instinct. When someone consistently dodges basic questions about their life, it’s not just mysterious, it’s isolating. You’re trying to build intimacy, and she’s keeping the scaffolding hidden. Here’s the move: don’t interrogate, but don’t tiptoe either. Tell her what you told me. That you care about her, that you’re invested, and that you’re starting to feel a little shut out. Frame it not as a demand for answers, but as a need for connection. If she’s not ready to open up, fine, but she should be able to say why, and reassure you that it’s not a red flag, just a closed chapter. And if she can’t do that? If the mystery stays sealed and the silence gets louder? Then you’re not being cautious, you’re being wise. Keep your heart open, but don’t ignore the part of you that’s asking for clarity. That part’s got good instincts. Uncle Gary