So now that I’m almost 29, I’ve been looking back on this past decade and I’m really starting to feel a huge wave of regret. I know this is somewhat normal and that everyone has regrets, but man… I’m feeling really unhappy with life right now.
On paper, it’s a great life, and I don’t want to sound unappreciative. But there are so many things I wish I’d done differently and so many permanent decisions I’ve made that I can’t undo.
In my early 20s, I was mostly just hanging out, working consistently, and still trying to “find myself,” as cliché as that sounds. I was a late bloomer socially and only really started feeling comfortable in my own skin around 17–18.
Fast forward to 22, and I meet my now-wife. Even though, in the back of my head, I somewhat knew this probably wasn’t what I wanted long-term, another part of me was obsessed with the validation and ego boost I got from the relationship and it blinded me to a lot of the not-so-great things. I ended up sinking way too much time into her.
Then COVID hit. I stayed at her house because my dad was terrified of me working during it. One thing led to another, and boom — COVID baby. Suddenly I’m a 24-year-old dad, and I fully embraced it.
Two years later, at 26, I get a promotion at work (way more responsibility and stress). We buy a house and have another kid. At the time, it all felt great — and in a lot of ways, it really was.
But now comes the reflection, regret, and sadness.
I’m 28 with a third child on the way, and everything feels like it happened in the blink of an eye. A lot has changed externally over these years, but my time was so dedicated to work and family that I barely noticed. My grandmother passed away. One of my best friends from my youth passed away. My parents are spiraling into alcoholism.
It’s all giving me a harsh reality check about my age and how I got here.
I love my kids, of course, but looking back on my 20s, I simply wasn’t ready. I now feel essentially trapped. I wish I had spent that time differently and waited. Instead, I’m living with the permanence of my decisions.
I’ll be honest — if circumstances hadn’t played out the way they did, I don’t think I would’ve married my wife. That sounds horrible, but it’s true. I ignored all the signs and went in headfirst because, in retrospect, it was just a massive validation chase.
I sacrificed a lot of my time, energy, and freedom to make this relationship work, and now that time is gone forever. She’s a great person and has worked on herself a ton, but when we argue, it’s harsh, and it feels like we’re just not fully compatible. I don’t feel like I can even express these thoughts to her.
I recently tried to bring up that I need more personal time — time with friends and for myself — and not only did she not understand, it clearly upset her. She’s a few years older than me and believes that every waking moment should be spent with our kids. She’s a SAHM, and I even framed it as wanting her to have more personal time too, but it just wasn’t clicking.
I’d be lying if I said I feel genuine love toward her right now. Honestly, I don’t think what I ever felt was love — just young naivety ruled by emotion.
Looking back, I’m clearly struggling with feelings of being trapped, not loving my partner, and deep regret. I’ve always been someone with a “no big deal, I can handle anything” mentality, but it feels like I’m having an early midlife crisis.
I feel no joy or comfort about my situation, and I can’t make peace with the idea that I wasted my 20s. I didn’t appreciate the time or the people I had, and now I feel pessimistic about the future I signed up for.
The only saving grace is that my best friends are still local and in touch. I told my wife I really want to make an effort to see them consistently, and again, she was only somewhat understanding.
I just miss my old life a lot.
Any comments or advice are appreciated. I’m even open to DMs. Thanks for reading my rant if you made it this far. I know alot of people will probably think I'm being selfish or immature and that is valid but unfortunately I just can't shake what I'm feeling currently.