Category: Advice Column

I’ve been with my girlfriend since I was 18—we were high school sweethearts. I’m 27 now, and she’s 26. After high school, I started working right away and have mostly been in service jobs. Right now, I work at the UPS Store. She went the college route, studied accounting, and is now a senior associate at one of the Big Four firms. She earns a lot more than I do, which honestly doesn’t bother me. I’ve never cared much about money in the relationship.

But when I brought up the idea of marriage, she said she doesn’t want to get married until I “establish” myself professionally. The thing is, I don’t have big career ambitions—and I’m genuinely happy with the work I do.

So now I’m wondering: has our relationship run its course? Are we just too different at this point?

Shes 60, single. I know how screwed she is, told her countless times, but she did it anyway. I don’t know how she’s going to survive on $1k social security a month and only $60k saved. No assets. No plan. Currently rents, which I help pay for.

I’ve been married to my wife (32F) for five years, and lately, I (33M) feel like I’ve lost any sense of freedom or privacy. It’s as though every day, she’s looking for something to be upset about, and I’m always walking on eggshells.

Take our finances, for example. While we share our money, we also have our own separate accounts. Yet, she logs into my account and questions every single purchase I make, even though we’re not struggling financially at all. I can’t bring myself to ask her about her spending habits because I’m afraid it will lead to a blow-up.

I (31F) have been friends with Sarah (31F) for over 20 years. We’ve been through a lot together—school, heartbreaks, careers, growing pains. She’s seen me at my worst, and I’ve seen her at hers. Neither of us has been perfect over the years, but recently… something shifted.

Sarah cheated on her husband.

They’ve since split, and the fallout has been painful to watch—especially because her ex, Alex, is someone our whole friend group loves and respects. He didn’t deserve what happened, and I can’t make sense of why she did it. She hasn’t reached out, and I haven’t either. I don’t even know what I’d say.

I’m 20 years old, and I want to be successful in life. I don’t just mean money (although that’s part of it). I mean I want to feel proud of where I am, be good at what I do, and not feel lost or behind all the time.

The problem is, I have no idea where to start. I scroll through Instagram and see people my age starting businesses, traveling the world, becoming “influencers,” or already in their dream careers. Meanwhile, I’m just trying to figure out what I’m even good at.

Sometimes I feel motivated, and I try to make a plan, but then I get overwhelmed. Other times, I just shut down and waste hours on my phone. I don’t want to drift through my 20s and wake up one day feeling like I missed my chance.

I’ve been dating a 34-year-old man for six months. One-on-one, we really click — we share similar values, traditions, and long-term goals. But I’m hesitant to introduce him to my family and friends because, in group settings, his behavior often comes off as cringey and immature.

He constantly brags about money, especially when comparing himself to people who went to university — I have a master’s degree, and he didn’t attend college. He’ll go on about how much wealthier he is than his family and how jealous they supposedly are, even though they seem like kind, normal people. I’ve gently tried encouraging more humility, but it hasn’t landed.

My wife’s been distant lately. We’ve had problems before, but this feels different. I tried to connect with her recently—nothing. I suggested we spend the day together, but she said she wanted to go to the library and work on her book.

Then she got dressed up—full makeup, perfume—and her phone lit up with a message from a guy I didn’t recognize:
“I’ll be waiting for you in bed. Bring me a coffee, please.”

Sometimes, out of nowhere, I’ll remember something awful I did years ago. It hits me like a punch in the chest. No matter how much time has passed, the guilt feels fresh. It’s not every day, but when it happens, it’s hard to breathe. Sometimes it even keeps me up at night.

I’ve tried forgiving myself. I’ve tried distraction. I’ve tried reminding myself that I’ve changed. But the memories still come back, and when they do, I feel like the worst version of myself.

How do you move on when your own mind won’t let you forget?

My younger brother (22) and his wife bought a house a few years ago for way too much money—at least according to me and my parents. They never even calculated their bills before locking themselves into a $2,000 mortgage. His attitude was always, “It’ll be fine.”

Right after that, they financed two $20k trucks, plus full coverage insurance. The problem? His job is seasonal, and he doesn’t pick up work in the winter. Eventually, they were about to lose the house and ended up begging our grandparents for $7,000. The deal was weekly repayments, but in six months they’ve only made one payment of $200.

Now he just told me he bought a camper—for $2,000—at the end of summer, while still owing my grandparents and facing another winter without steady work. On top of that, they’re trying to have a baby with fertility treatments.