Women Share Their Biggest Dating Regrets From Their 20s

Let's face it, whoever said that our 20s were our prime years was very wrong. In reality, our 20s were no different than our teen years. It was a time of finding our identity, settling in our careers, and dating all the wrong people. It's a time for learning and discovering.

With that comes a lot of regrets and embarrassing stories. Thankfully these women admitted it on our behalf so that we can all laugh together.

From "Left On The Shelf" To "Happy And Single"

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Photo Credit: Brooke Cagle / Unsplash

The expectation is that we'll be married by a certain age and have children by another age. We're afraid that if we don't hurry to find a partner, that we'll get left behind. So like this woman, we settle for the wrong people to fit the role.

"Then I met an old work colleague. She was five years older than me and I got my life mantra from her - 'I’d rather be single and happy than together and miserable' - and I’ve never looked back. I own my own business, I own my own home, I am financially independent. " SleepFlower80 / Reddit

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Staying Too long In The Wrong Relationship

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"Giving people chances because they’re 'such a nice guy.' If the spark isn’t there, it isn’t there. All the extra time did was it make apparent why the spark wasn’t there in the first place." - Confetticandi / Reddit

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The real regret here is thinking of how that time could've been used more productively. It wasn't exactly wasted but it could've been used to create better memories.

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Only Settling For Those Who Were Already Interested

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"Dating people who were interested in me instead of pursuing people I was interested in. It was so lazy." - Connie_Damico / Reddit

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This was something we did to protect ourselves, but also because it was more comfortable. It took away the risk of coming off vulnerable and then getting rejected.

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Giving Players The Time Of Day

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"Giving players my time/attention when they don't reciprocate. It took two years for me to finally let one go. It was either I see him when he was free or I don't see him at all."

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Too many times we waited on someone's text and let the whole day be ruined when they canceled on us. It takes time to realize that we're the ones in control.

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Living To Please Others

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"Doing 'the right' thing. Going to college, getting married to my first serious boyfriend, getting a career, buying a nice house in the suburbs, all in that order."

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"I didn't live for myself not one minute. I lived to please other people and did what I thought you were supposed to do." - Whiskthesofa / Reddit. It's not easy to put yourself first even in relationships.

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Not Taking The Time To Explore Many Relationships

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" I regret not dating enough, not realizing that quality men would completely disappear shortly after." - keights101 / Reddit

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Each partner teaches their own lesson. However, although maybe the odds of finding someone are slimmer when we're older as couples get married off.

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Being The One Hurting Others

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"That I cheated and hurt so many people. In my 30s now and I'm deeply ashamed of how I’ve treated most of my ex’s in my 20’s." - messyaurora / Reddit

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Being in our 20s is a time to also make our own mistakes. It's okay to admit that we were the ones doing the hurting of others, and using it as an opportunity for growth.

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Lust Is Not The Same As Love

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"Sex does not equal love. Or even like. Just because a guy has sex with you, even regularly, doesn't mean he truly cares about you." - BitterPillPusher2 / Reddit

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It's easy to mix the rush and excitement of lust with love. It's not until it wears off that we're able to learn the signs to differentiate the two.

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Giving Cheaters Second Chances

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"Giving a cheating boyfriend a second chance. Never again. Cheat once and I'm gone for good. Don't even want to hear an apology." - Reddit

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Forgiveness should be earned. Often it's only by experience that we learn that some people won't ever change or put in the effort to try and fix their mistakes.

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Always Trying To Seem "Cool"

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"Being the 'cool' girl because I thought I wasn't worth basic respect." Instead, this is her advice for everyone in their 20s — "If someone leaves you because you want respect, then they are not worth it."

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There is a basic level of respect that should be the expectation. Accepting to be treated for any less is a disservice to ourselves despite how much we love that person.

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Not Being Honest About Our Needs

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"I spent an embarrassing amount of time in college crying over some person I was casually seeing because I started liking them a lot more than they liked me, and I wanted to date them but they made it clear they weren't looking for anything serious." - promises_in_progress / Reddit

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Many of us felt helpless to hook up culture that we agreed to give up our needs for relationships that made us feel worse than being alone.

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Believing Words Over Action

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"Believing what people were saying instead of what they were doing. Talk is easy, but people who follow-through are a rare breed." - miss_micropipette / Reddit

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It's okay, we're all guilty of believing empty promises and continue living for the hope of the future. Eventually, reality sets in and we realize there's no point if we're not happy in the now.

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Trying To Fix And Mother Our Partners

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"I was definitely Miss Fixit and it's something I want to leave behind. I have had a tendency to lean into more of a parent than a partner role and not have my partner be able to stand on their own." - coastalkid92 / Reddit

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Partners shouldn't need a second parent or to be someone's project. it's important for them to take the time to work on themselves first.

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Needing A Partner In The First Place

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"The idea that I needed a partner at all. If it happens, cool. If not, also cool. You don't need a romantic partner to be happy. And if you do, then you need a therapist, not a romantic partner." - BitterPillPusher2 / Reddit

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Partners aren't supposed to fill a void. In order to truly be happy in a relationship, we need to be happy alone first.

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Not Speaking Up And Standing Up For Ourselves

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"I am annoyed at myself for letting so many things slide and it just led to built-up resentment. I've made myself a promise that from here on I will be more open and clear on what I want and how I feel about things!" - GoonerGirl9 / Reddit

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We may have thought we were avoiding arguments or being the bigger person, but little did we know, every issue that was unaddressed had a way of coming out.

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Getting Married Before You're Sure

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"I was married at 23, and while I don't necessarily regret it because it shaped who I am now, it made me off the market to meet so many other people."

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"He ended up having an affair and tore my family apart. Now I’m 27, divorced, back on the market and starting over. " - pomchimom / Reddit

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Feeling Pressured To Always Say Yes

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"I should've been more firm and not be a "yes girl" just for the sake of impressing a guy and hoping he’d like me more."

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"I remember he texted me at 9 pm to come hang out with him and his friends. I was already showered and in bed. Here I am texting him back, “Sure!” even though deep down I wanted to say no." - trwwy321 / Reddit

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Getting Stuck In Codependency

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"Live alone for a while. Make sure you are independent before getting too committed. It's too easy to become dependent on someone when you are young." - Irritabl / Reddit

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If we don't know what our goals, needs, and values are before committing to someone, we're likely to simply attach ourselves to theirs, and lose our own identity.

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Looking For Someone Who Shared Our Exact Mentality

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"Looking for someone who shared the same point of view of the world as I did. Very negative. It just kept me in that frame of mind and engulfed me." - FoxyVel / Reddit

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Part of the beauty of relationships is the perspective they bring. The right partner encourages us to step outside our box to find new experiences. That's how we grow together.

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Not Knowing Our Worth

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"I took care of a boyfriend financially for most of my twenties. I focused on him instead of my own personal development. Now that I'm nearing 40 I have a lot of regrets." - kalliemist/ Reddit

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This may be the biggest lesson of all. It is the reason behind why we let ourselves get into all kinds of toxic relationships. Once we know our worth, we know what to look for and that comes with age.