Advice Column

We’ve been together for six years. In our third year, I cheated on him with a close family friend because I took him for granted and didn’t value the relationship. He broke up with me for months, but when I realized how much he meant to me, I begged him to take me back. He agreed on the condition I never speak to that guy again. Since then, I haven’t cheated or been tempted, and I now see how great a partner I have.

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Is it just me, or does it feel like modern work is a giant scam? Most days, I’m sitting at my desk feeling like I’m just helping someone else get richer while my own life slips by. The harder I work, the more I realize the system is rigged: a few people at the top win big, and the rest of us are left scrambling for scraps.

All those motivational posters about “climbing the ladder” just sound like a bad joke now. I’m not climbing anything—just trying not to get buried under bills and burnout.

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I’m a 28-year-old guy, and my girlfriend of six years just told me she said “I love you” to another man—let’s call him Tim. They work together and have become close over the past year. Tim’s confessed his feelings before, but this weekend she finally told him she loves him too. They cried, talked, and held hands, but she insists nothing else has happened, and I believe her.

I know it’s possible to care for more than one person, and I’ve had crushes too, but I don’t act on them or let things get this far. Now I feel like I’ve been emotionally cheated on. She says she still loves me and wants to stay together, but everything feels different now. I’m torn between breaking up or trying to move forward, but I honestly don’t know what to do. Any advice?

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I’m a 35-year-old guy and, to be honest, I’ve been feeling really lonely lately. I never had a girlfriend, dating feels impossible and I don’t have much of a social life these days. I work from home, most of my friends have moved away or are busy with their own families.

I’ve read about “professional cuddlers” you can hire to cuddle with. Part of me feels kind of embarrassed or ashamed for even thinking about paying someone for basic human contact, but another part of me just wants to feel connected to someone, even if it’s just for an hour.

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Hello, I (32F) have the opportunity to go on a international vacation on my own. I have travel credits I need to use and going on a solo vacation has always been on my to-do list. I am also a mom of 2 and my husband (36M) is encouraging it.

I just recently found out my friend (30M) will be also doing a solo trip and going to see a concert where I was wanting to go. I think it would be awesome if I could fly with him there, see the show and then part ways.

I talked to my husband and he is okay with it although I’m worried about what other people will think, especially my in laws and my parents “why would she go on vacation with another man?!” But I don’t want to have to explain myself over and over.

Input on whether this is appropriate?

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I am a six-foot-tall guy, in good shape, late twenties, decent looking, have a good job, take care of myself. On paper, it seems like I should not have a hard time dating. But I cannot even get a date. Not a single one. I try apps, I ask women out in person, I try to meet people through friends—nothing. Just constant rejection or, at best, being told I am “such a good friend.”

The part that really gets to me, though, is seeing guys who are honestly not attractive—guys who are shorter, out of shape, kind of awkward, whatever and walking around with girlfriends. I am not trying to sound cruel, but it makes no sense to me. I see couples all the time and I cannot help but think, “How did he pull that off?” It is like they have cracked some code I just do not get. Meanwhile I am out here doing everything right and getting nowhere.

Is there something I am missing?

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I’m 21F and have been with my boyfriend (22M) for four years. Since finishing high school, he’s barely worked—just one summer job. He doesn’t want to go to college or get a regular job, saying he hates the idea of working for someone else. He streamed online for two years, then half-heartedly tried starting a business, but nothing ever came of either. Mostly, he plays video games all day and says jobs just don’t feel right.

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I support trans people and I support my husband being his/her true self but it’s so hard and I don’t know if I can do this.

I’m attracted to men especially the man I married but he’s going to be a woman now and I don’t find that attractive on a physical or emotional level so I feel really heartbroken and I don’t know how I’m going to explain it to our family, our friends or especially our children.

Again I want to be supportive if this is my husband’s true self but I don’t think our marriage can survive this because of my own preferences etc. It’s just so difficult and honestly I don’t know what to do…

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I’m 45, and I feel like I’ve screwed up my financial life. I make decent money (about $80k a year), but between raising kids and just not paying attention, I barely have $40,000 saved for retirement. Every time I see something about how much people my age should have, I feel sick to my stomach.

I want to catch up, but saving a few hundred bucks a month feels hopeless at this point. I keep reading about people making a killing in crypto or day trading, and honestly, it sounds tempting. I know it’s risky, but the idea of doubling or tripling my money fast is way more appealing than grinding away for the next 20 years and still coming up short.

Am I crazy for even thinking about this?

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My girlfriend recently started her Master’s and has been hanging out with a group of friends from college, including some guys. I never thought much of it, but last weekend, I asked if any of the guys had hit on her. She initially brushed it off, but then admitted that one of them asked if she had a boyfriend. She told him yes, and he said it was too bad because he and others had been wondering if she was single. She didn’t tell me right away because she didn’t want me to get paranoid.

[Read more…] about “My girlfriend let a guy that likes her sleep in her bed.”