It’s easy to get swept up in what everyone else is doing when you’re in your 20s. In the moment, a trend can seem harmless: a haircut, a daily ritual, a way of thinking. But years later, many women will look back and wonder why they ever thought it was worth it in the first place.
Some regrets aren’t about embarrassing photos or naive mistakes. Sometimes they’re about wasted time, or energy that you’ll never get back, or trying to be someone you didn’t feel like you really were. These are the quiet regrets, the ones that you don’t really shake for years, if ever. These are the regrets that make you take a different path forward.
Here are 11 trends women say they regret following in their 20s.
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Trying to Be the “Cool Girl” Who Never Needs Anything
Acting like you didn’t need anything became a secret competition. It was all about being “so chill,” even when you weren’t. Women later looked back on playing small or hiding their needs to get validation they didn’t even care about in the first place. And it only taught people to take you for granted.
Jumping Into Trending Side Hustles
The idea of starting a business or side hustle with your own online shop was empowering, until you realized most of it was really just stress in a cool costume. Juggling orders at 2 AM and selling at a loss to gain some following was fun? Girlbossing yourself to death was not at all the fun it was cracked up to be. You felt like you traded sleep for superficial hustle points.
Accepting Messy Friendships as Normal
For a while, friendships that were hot and cold or up and down were normal. Volatile, turbulent, or roller coaster friendships felt deep and passionate. But constantly having to fix things or tiptoe around drama wasn’t actually a form of closeness. It was exhausting. Peaceful connections later on felt like what was actually missing.
Over-Exercising as a Coping Mechanism
Going hard at the gym five times a week wasn’t always healthy. Sometimes it was to cope with anxiety, insecurity or pressure to fit a mold. It wasn’t the exercise that was regretted but hiding behind fitness instead of facing internal battles.
Living With Terrible Roommates
Sharing a trendy zip code seemed worth the sacrifice at first. But loud parties, late rent payments, or passive-aggressive notes quickly added up. With hindsight, many would have chosen peace and a longer commute over trying to be “cool city dwellers” with terrible roommates.
Staying in Jobs That Had Prestige but Zero Respect
The company name looked great on a resume. The office was sleek, the title sounded nice, but the culture was toxic. Women worked longer than they should have because they thought suffering was just part of the process. Years later, they saw that dignity was worth more than any LinkedIn badge.
Keeping Quiet About Weird Dates Just to Be Polite
There was this weird pressure to not be seen as “mean” or “too picky.” Even if someone’s actions were so obviously disrespectful or wrong, some women just went on second (or even third) dates just to “keep the peace.” They regret this now.
Saying Yes to Trips They Couldn’t Really Afford
FOMO was real in your 20s. So when your friends decided on that spontaneous trip or birthday weekend getaway, saying no to the plans felt impossible. But the credit card bill, the stress of falling behind on rent, and the lack of presence during the trip were not as fleeting as the trip itself.
Letting Social Media Dictate Their Milestones
Seeing other people get engaged, promoted, or pregnant made you feel like you were always playing catch up. But regretting not having those things wasn’t the issue. Allowing complete strangers’ timelines to shake your confidence in your own journey was.
Chasing Emotionally Unavailable People Like It Was a Challenge
There was a strange thrill in trying to be the person who could change someone. It felt like a romantic movie plot until it didn’t. Years later, many realized they were ignoring people who were ready and kind in favor of chasing someone who could barely communicate.
Wearing Outfits They Hated Just to Fit the “It Girl” Look
You put up with all the ugly crop tops, the shoes that had to be wrestled into place every time you tried to walk in them, and the skinny jeans that you couldn’t actually breathe in. You wasted so much time trying to squeeze into the body and keep up with fast fashion cycles. You can live without those clothes, but the fashion mistakes you regret are mostly about not listening to your gut.
Disclaimer: This list is solely the author’s opinion based on research and publicly available information.
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