Advice Column

I recently asked my husband how he felt about our relationship, and during a difficult but honest conversation, he admitted something that shattered me: he wishes he had accomplished more in life, but feels it’s too late now. He looked so tired and defeated when he said it. I haven’t stopped crying since.

He’s not unsuccessful, just not where he once hoped to be—and I’ve always believed in his potential. Now I’m overwhelmed with sadness and guilt, wondering if I held him back. I wish I could go back and tell the younger version of him that life is still full of possibilities. I’m sorry if my own emotional struggles—depression, anxiety, postpartum—kept me from being the partner he needed. I feel like I dragged him down.

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My wife and I have been married for five years, but our relationship has had its struggles. About a year ago, I reconnected with an old friend from after high school, and we started spending time together as couples. During that time, his wife made a pass at me, and we’ve been having an affair for the past eight months.

We’ve talked about everything—our marriages, our frustrations, even the possibility of being together.

But now I’m torn: Are my feelings for her real, or is this just the excitement of the affair?

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My 18-year-old son was thriving—not only excelling in a competitive sport with Olympic potential, but also socially and academically. That all started to unravel after he began dating his current girlfriend.

Since meeting her, he’s isolated himself from friends and family, dropped out of high school, and stopped training seriously. He now spends most of his time either waiting for her outside her school, walking her to and from class, or being glued to his phone talking to her. If he doesn’t comply, she calls him crying, yelling, and manipulating him emotionally.

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I recently started a new relationship, and things are going well—we’re still in the early stages, but there’s real potential here. The complication? I still have a huge collection of photos from my previous relationship. My ex and I were together for six years, and we traveled a lot, so I’ve got around 20,000 photos scattered across my phone, laptop, and hard drives.

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I’m in my mid-20s, pursuing a master’s degree, and building my career. My boyfriend, who I love deeply and who treats me better than anyone I’ve dated, is unemployed, hasn’t finished his degree, and lacks ambition. He says he wants the same life goals—financial stability, travel, a good career—but does little to work toward them. I have to push him just to apply for jobs, and he always has an excuse to delay it.

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I’m a 43-year-old mom, and my 16-year-old son, Ryan, has always been a stereotypical “jock”—he plays football, is popular at school, and has had the same best friend, James, since they were kids. James is like family: they go to the gym together, drive to school together, have sleepovers (only with each other), and even vacation with us.

Recently, due to a string of neighborhood robberies, we installed a Ring doorbell camera. Yesterday, after coming home from the gym, I caught something on the footage that surprised me: James and Ryan kissed on the front steps before James drove off.

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I’m a 26-year-old woman, and I’ve started to accept that I’m considered “ugly” by society’s standards. It feels like this affects how people treat me, and it’s hard not to take it personally.

At a recent church picnic, no one greeted me or tried to include me. One man spoke to me in a dismissive tone when I looked into a cooler, so I deliberately took my time choosing a bottle of water just to push back a little. Later, when I tried to make room in a tent during the rain, I apologized for being in the way, but the woman I apologized to ignored me completely.

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Two months ago, my grandmother legally transferred ownership of her house to me. She’s still alive, but due to her declining health, she wanted to ensure the house went to someone she trusted. My father is furious. He claims the house should be his and has given me an ultimatum: return ownership to my grandmother or he’ll cut all contact with us.

Here’s the context: When I was nine, my dad left us after remarrying and didn’t offer support—emotional or financial—for over a decade. He only returned last year after his second marriage fell apart and he lost his job. Now, he and his wife are apparently reconciling and planning to sell the house, which is how he discovered the ownership change. He says I’m untrustworthy and accuses me of putting the family at risk of homelessness.

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I moved in with my girlfriend, and I regret it. She gets angry over small things, and no matter how much I apologize, she won’t talk things through. When I tried to express how I feel about her lifestyle, she got upset again. Now I feel like I can’t say anything without triggering a fight.

The problem is, our rental contract locks us in for two years. If we break the lease early, we’ll have to pay a fee. So even if we break up, I still want to stay and live with her—just as roommates—until the lease ends. I just need advice on how to make this situation more livable.

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My husband and I got married in 2017. We both came into the marriage with separate assets, and we signed a prenup that stated whatever we brought in would remain individually owned. At the time, this felt fair and safe, especially for me — I had a significantly higher net worth, and I’ve been through a financially abusive relationship before. That prenup gave me peace of mind.

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