10 30-Somethings Reveal The Biggest Relationship Regret Of Their 20s



“I spent so much time beating myself up for being single in my 20s, and that was such a waste of time. I’m now engaged (at the age of 36) and my husband-to-be and I are going to try to have children pretty much immediately. I come from a very conservative family, and they put a lot of pressure on me to get married and make babies early in life. Look, I was trying. I was definitely interested in meeting someone in my 20s, but when it wasn’t happening for me, I got horribly depressed. Yes, I’m happy about finding someone to spend the rest of my life with, but I had to accept myself and realize I was not only valuable because of my child-bearing capabilities before I found my future husband. I love my family, but I resent that they made me feel like I needed to get married and have a family by 25 to be of value to the world. That’s bullshit.”

— Amanda, 36


“I wish I were kidding about this, but I wish I hadn’t been such a snob about location when I was dating in my 20s. For a while, I lived in Williamsburg, and I swear, I dated exclusively in Williamsburg and the East Village because, well, proximity. I live near the Flatiron Building now, and at one point met a great guy who lived in Queens. It’s not that I have anything against Queens, but when would we see each other? It would take me an hour and a half to get to his apartment after work. I didn’t give it enough of a chance, and that was the case with many of the people I dated. I’m still dating, and looking back, I should’ve at least put in more of an effort. It’s something I’m working on.”

— Karley, 32


“I honestly don’t have any regrets. I broke off an engagement when I was 27 and I am absolutely not sorry I did it. It takes more courage than you think as a 27-year-old who wants kids to walk away from a secure relationship. But I knew it wasn’t there — that ‘thing’ that you’re supposed to feel, so I had to walk away. I am one of three people in my 12-person friend group who isn’t married and it’s hard to know that I decided against what they have. But, at the end of the day, I do not regret anything because I know I made the right choice.”

— Amanda, 34


“I got married at 24 and I knew nothing about money. I’m 30, I just stopped working because we just had our first child. I’m 100% aware that I’m not contributing to our finances, and I don’t know anything about that side of our life. I feel like I’ve relinquished power, not because I’m staying home with our child, but because I don’t know anything about our money. I don’t know how our retirement accounts are doing, or whether we can afford the premium-brand diapers for our child. I don’t regret getting married, or having a family, but I regret that I wasn’t prepared. I was so young and unaware when I got married. I needed to know so much more, and I still do.”

— Maria, 31


“I regret not going out to meet people more in my 20s. I had an awful work/life balance throughout my 20s. I made really good money, but I worked like a dog — 13 hour days, etc. — and I wasn’t treated well. I was so burnt out, that when liked people and wanted to ask them on dates, or when my friends wanted to bring me to a party, I always said ‘no’ because I was too damn tired. It’s not that I’m upset that I didn’t meet my one true love, I just think that I owed it to myself to make more of an effort to have a personal life.”

— Jared, 35


“I wish I had let more people set me up. So many people offered, but I was uncomfortable with the fact that I wasn’t finding my own dates, and I just felt so weird about letting other people find women for me to date. But, honestly, what did I have to lose?”

— Ben, 32


“I should’ve slept with more people. I’m in a domestic partnership with my guy, we’ve been together for six years, and I’m thrilled that we’re still very happy together. But, like, I could’ve fucked a lot more people in my early 20s.”

— Lia, 31


“I let my girlfriend cheat on me for six months before calling her out. I’m single now, and I have been for a few years, because she really messed with my head. I regret allowing her to take advantage of me for so long because I thought we were ‘meant to be’ and that she’d grow out of the whole ‘cheating on me’ thing. She didn’t.”

— Alexis, 34


“When I was in my early and mid-20s, I was with a woman I loved, but who I knew I didn’t want to spend the rest of my life with. We lived about two hours away from each other, and even though we’d discussed the fact that we weren’t going to end up together, we took the ‘but we’re in love now’ approach and stayed together. We were together for six years before finally breaking up. Six amazing years, but ultimately, six years too long. I wish we’d listened to ourselves and been realistic about the fact that we both wanted marriage and weren’t going to marry the other person. I know we should’ve ended our relationship earlier.”

— Robert, 36


“When my boyfriend and I met in college, we were sure we were made for each other. Most of our relationship was long distance: I studied abroad, we had a semester together, he studied abroad, and then after a summer together, we both took jobs in different places. Two years later, we got married and moved in together. Looking back, there was so much we needed to know about each other. We divorced after eight months. We were both divorced by age 26.”

— Jenn, 33 Thought Catalog Logo Mark

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Maya Kachroo-Levine

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