I was laid off last month...

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,

I’m a 65-year-old woman...

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 feel this weird mix of joy and jealousy.

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,

I recently started dating a guy...

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

I just started an amazing job...

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

Dear Uncle Gary, I met my wife when I was 18....

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.

I'm recently out of a twelve-year relationship.

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.

I'm 23, still living at home

Dear Uncle Gary, I'm 23, still living at home and going to school, taking a full load and working part-time. Is it selfish to want space from my own family? Signed, Leave Me Alone Dear Leave Me Alone, You’re not selfish. You’re human. You’re juggling

How do I forgive someone who isn’t sorry?

Dear Uncle Gary, How do I forgive someone who isn’t sorry? Signed, Disappointed Dear Disappointed, Let me start here. Forgiveness is not a performance. It’s not a handshake a ceremony, or a public declaration. It’s not about letting someone off the hook. It’s about letting yourself

If nothing changes today, where will you be in ten years?

Take a moment and a deep breath. Look at your life right now. If nothing changes today, where will you be in ten years? Be honest with yourself. The words that follow are meant to be a wake-up call. You can either read them and be motivated to act, or

Why Uncle Gary?

This picture means more to me than I can put into words. That's my nephew, who we lost too soon, and my niece, who still lights up every room she walks into. They're the reason Ask Uncle Gary exists.