Advice Column

Two years ago, my brother won the lottery. Like, literally won $3 million. Just a regular ticket he picked up at a gas station. I remember he called me, laughing and crying at the same time. I was happy for him. I really was. But ever since then, something in me has started to rot.

He and his wife used the money wisely. Paid off debts, bought a house outright, helped out our mom by clearing her mortgage. They put a bunch into investments, and now they’re basically done with the whole “working full-time” thing. She stays home with their kid. He works maybe a day or two a week, just to keep from getting bored.

And I’m still here. Grinding.

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Over the last few months my girlfriend and I have had a few fights over how I talk to her. I didn’t recognize it at first but the more I become aware the more I see it.

It seems like anytime there’s any issues or any amount of tension, no matter how little, between us I just blow up and scream at her.

I don’t mean to do it that’s just how I always talked to my parents growing up as they would constantly scream at me.

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I’m nearly 40, divorced. I live with my mom, in a kind of mutually beneficial arrangement- I pay the mortgage, which is like…. 1000 dollars a month…. And I don’t have to pay Los Angeles rent. But she needs me there because otherwise she can’t keep the house.

So, I’m working. The job is just a job. Pays well but not well enough to live in LA and pay rent and have headroom. I can’t really leave. I also just do not care about my work and I’m phoning it in. And the world is falling apart.

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I’m facing a tough future with Social Security—looks like I’ll get about $650 a month at age 67, and it doesn’t seem possible to raise it much. I have 32 years of work history, three zero-income years, and nothing to show except some small self-employment income.

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I’m at a loss. My wife (31F) and I (35M) have been together five years and have two young kids. Early on, I caught her sexting and talking to men online. She’s always had kinks she was embarrassed about, which she now explores with sex workers on OnlyFans. I tried to set boundaries but eventually allowed it, figuring at least she wasn’t hiding anything. I’ve done everything I can to fulfill her fantasies, but she constantly critiques me. My confidence is shot. Every other partner I’ve had was satisfied, but nothing I do is ever good enough for her.

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I’ve been the side chick for over five years.

I didn’t even know he had another girlfriend until about two and a half years in. By then, I was already head over heels—lost my virginity to him, thought I’d marry him. I was young, he was older, and I fell hard. When I found out, I couldn’t bring myself to walk away. So I stayed.

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My wife recently told me she wants to have dinner alone with one of my close male friends because they “get along well” and she values their friendship. I told her, calmly and respectfully, that I’m not comfortable with that. It’s not about jealousy or a lack of trust—I do trust her. But to me, having one-on-one dinners with someone of the opposite sex (especially a friend of mine) crosses a boundary I believe should be mutually respected in a marriage.

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I’m short, I have been specifically told that I was too short to date multiple times. I’m fairly average in looks but I am short. The vast majority of girls won’t date a short guy unfortunately, all I’ve heard from girls is “tall dark and handsome” I’ve never met a girl who preferred to date short guys and only met a couple who didn’t mind.

Being short is one of the most unattractive traits a guy can have and people will always remind you of that with jokes, insults, mocking and condescending comments. Dating as a short guy is almost impossible, I just give up.

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Your health is essentially on the decline by the time you reach 40, and by the time most people reach their 60s they’re already on a cocktail of medications, lacking the energy to do most things they used to do regularly, and also have a plethora of new health problems to deal with until they finally die.

Most retired people I’ve met typically consider a trip to Costco or falling asleep in front of the nightly news as the highlight of their day.

Some even started working again, albeit part time, just to fill their lives with something productive or meaningful.

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