Hey Uncle Gary, I just started dating a man who has only a couple of close friends. My friends say it's a red flag. Should I be concerned that something is weird about him? Signed, Concerned

You are always welcome at All Saints Pasadena

Dear Uncle Gary, My stepmom keeps introducing my husband as my “friend.” Not once, not twice, every time . We’ve been married for over two years, and it’s not like she doesn’t know. She was at the wedding. She’s met his family. She’s seen the ring. At first, I brushed it off as forgetfulness or awkwardness, but now it feels intentional. Like she’s minimizing our relationship, or refusing to acknowledge it. It’s starting to feel disrespectful, not just to him, but to me as wel

Dear Uncle Gary, I (25F) love my boyfriend (27M). We recently talked about exploring our sexuality, including swinging or threesomes, and admitted we’re both bi-curious. I told him I’d support him if he wanted to explore, as long as it was safe and honest. The very next day, he met a man from an app and had sex. Afterwards, he told me he enjoyed it in the moment, but doesn’t want to do it again. He says it felt unnatural, he doesn’t think he’s bi, and he never wants to play w

Dear Uncle Gary, I have a question that feels a little unusual, and I haven’t met anyone, or even heard of anyone, in quite the same situation. Is it normal for me not to orgasm during sex? I genuinely enjoy being intimate with men. I’m a bottom, and I feel confident in what I bring to the experience. The pleasure itself is wonderful, yet I’ve never had a partner who could make me ejaculate. With toys like Fleshlights or other masturbators, I have no problem reaching climax,

Dear Uncle Gary, I’m 59. A mother, a wife, a teacher. My life is steady, even lovely, two grown children finding their way, a marriage that still feels like home. I’ve lost people, yes. Parents. A sibling. But grief becomes a quiet companion at this age, doesn’t it? Today, though, today something cracked open. I was walking, nothing unusual, and the autumn leaves were turning gold, crimson, rust. And I just… cried. Not from sadness exactly. But from the sheer beauty of it. Fr

Hey Uncle Gary, Out of all your married friends, how many would you say are genuinely thriving in their relationships, not just sticking it out, but actually happy and fulfilled? Signed, Curious George Hey Curious George, All of my married friends seem  happy, but happiness isn’t a fixed state, and appearances don’t always tell the full story. Relationships ebb and flow. Even the strongest marriages go through seasons of joy, frustration, distance, and reconnection. If happin

Dear Uncle Gary,    I’ve been dating my boyfriend (28M) for about a year. Things have mostly been good; we work out together, take little trips, and I’ve tried to be the supportive, non-controlling girlfriend, especially since he told me his ex was the opposite. Lately, he’s been spending more time at the gym, which I didn’t think much of. But a few days ago, while I was using his phone for music, I saw a message from his gym buddy. When I asked about it, he grabbed the phone

Dear Uncle Gary,    My wife and I have a blended family with five kids. Before she passed, my late wife asked me to protect a portion of her medical settlement and savings for our son. I’ve honored that promise and continued saving for him separately. Now my current wife wants us to lay everything on the table, what each child has saved, and consider combining all funds to divide more evenly. I’m open to discussing what she and I have saved together, but I won’t include the m

Dear Uncle Gary, How do I tell this guy he gave me an STI?    We haven’t spoken in about a month. I ghosted him. Over the weekend, I got tested because I thought I had a yeast infection. Turns out, it’s chlamydia. He’s the only person I’ve been with, so I’m certain it came from him. Now I need to tell him, but I have no idea how to break the silence and say, “Hey, you need to get tested.” What’s the best way to do this without it turning into a fight or a guilt trip? Signed,

Uncle Gary, My wife hit me with a question that stopped me mid-sip: “If women have the 6-6-6 checklist, six feet tall, six-figure income, six-pack abs, what’s the male equivalent?” In other words, do men have their own shorthand fantasy for the kind of woman they want to date, something equally superficial, equally viral, equally absurd? Signed, My Wife Wants To Know Dear, My wife wants to know, Oh, absolutely. Men have their own version of the 6-6-6 fantasy; it’s just not as

Hey Uncle Gary, So I went on this date. It was fun, he picked the spot, we had great convo, dinner was amazing. Afterward, we played pool at a bar around the corner, and he walked me back to my apartment. I kissed him goodnight. It felt sweet, like maybe the start of something. I was hoping I’d hear from him the next day… maybe a “had a great time, let’s do it again.” Instead? Boom. A Venmo request. Half the bill. I was honestly shocked. I always thought if a guy asks you out

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 apol

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, so

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 c

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. Not

Dear Uncle Gary, I told my date I don’t believe in soulmates. She said, ‘That’s so sad.’ Is it? Signed, So Sad Dear So Sad, Not sad. Honest. Believing in soulmates is like believing your perfect pair of jeans is out there somewhere, waiting to hug your thighs and never betray you. It’s romantic, sure. But it’s also a little lazy. It assumes love is found, not built. What you said, I don’t believe in soulmates , isn’t a rejection of love. It’s a vote for choice, for effort, fo

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 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