Category: Advice Column

I’m 27 now, and I keep replaying all the cringey things I did in my early twenties. I’m talking about getting too drunk, making a fool of myself, and honestly just not being the best friend or version of myself. It feels like I have to learn everything the hard way.

Sometimes I said or did embarrassing things. Sometimes I drank too much at work events. Sometimes I was just plain annoying to be around at night. Looking back, it makes me cringe.

The thing is, I’m actually proud of who I am now. All those mistakes shaped me into the person I am today. But I still have trouble forgiving my younger self. I keep wondering—how did I not know better?

Last week was a disaster for my coworker, “Maya” (30F). She came into work seeming confident and content, but hours later, her brother Evan (26M) fell off the roof of his house. He was conscious afterward and apparently felt fine, so he didn’t call emergency services. Tragically, he had serious internal injuries and died.

I was shocked and heartbroken for Maya. I can’t imagine losing a sibling. But after hearing what happened, I also found myself thinking Evan had been reckless. Why was he on the roof? And after falling, why didn’t he call for help just to be safe? If it were me, I would have, especially knowing how devastated my family would be if something happened.

I’m 27 and engaged to my fiancée, also 27. We’ve known each other since high school, started dating in 2025, and are supposed to get married next August. Most of the time, our relationship is loving and we handle disagreements calmly.

But I have a problem with how I act when I get extremely frustrated. I’ve punched walls, thrown things, and kicked furniture. Recently, after a stressful day, I threw a lawn chair across the yard. My fiancée told me I could never behave like that again. That matters even more because she was previously in an abusive relationship.

My husband and I have been married for 12 years, and we have two young children. Around the time we got married, he started a business and went all in without discussing it with me first. For about eight years, the business was extremely profitable. It grew to more than 20 employees, several stores, and a small factory.

At the time, I also had a high paying job. After I became pregnant, I changed careers and worked part time so our family would have health insurance. Most of my income went toward groceries. We lived frugally with his parents and saved a significant amount of money. But my husband also moved money into accounts I cannot access. I do not even know where those accounts are or how much is in them.

I’m 27M and have been dating my girlfriend, 25F, for about six months. Things have been going well, but we recently had an argument about boundaries, and now I’m wondering if I’m being unreasonable.

In my previous relationship, my ex and I agreed not to spend time one on one with friends of the opposite sex or maintain close friendships with them. She stopped talking to a few male friends she had previously hooked up with or who had expressed interest in her. She also limited nonwork conversations with male coworkers. The only male friend she remained close with was gay because neither of us saw him as a potential romantic threat.

My wife and I have an 18 month old son. We split childcare roughly 60/40, with her doing a little more. I cook, she cleans, and I contribute more financially. Her business only requires a few calls each week, while mine is in an active growth phase and usually requires 10 to 12 hours of work a day.

I mention all of that because we are both involved parents and contributing partners. The problem is that my wife sometimes has extreme reactions to minor inconveniences. Some weeks she handles stress perfectly well. Other times, the smallest problem can cause a complete meltdown. I often feel like I am walking on eggshells, trying to anticipate what might set her off.

My wife and my family have never really gotten along. Whenever there is an argument, my wife expects me to take her side. Most of the time I do because I am her husband and I do not want her to feel like she is alone.

Recently, though, something happened that made me rethink that.

My partner, 36M, and I, 31F, have been together for four and a half years and were friends for several years before that.

He works in tech and I work in education, so he was already earning more than me. Two months ago, though, he accepted a new position that more than doubled his salary. He now makes almost three times what I do.

My girlfriend and I kissed on our third date when we first started seeing each other. That night, we became intimate, and about two weeks later, we had sex for the first time. She was a virgin, and I was her first sexual partner.

We have now been together for a year and three months. Our relationship is great, and I genuinely believe she is someone I could marry. But there is one thing I cannot seem to get past. I keep thinking about how quickly she trusted me and became intimate with me.