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”

woman makes silly face and smiles
Photo Credit: Brooke Cagle / Unsplash
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

Staying Too long In The Wrong Relationship

couple holding hands wrapped in string lights
Photo Credit: Anastasiya Lobanovskaya / Pexels
Photo Credit: Anastasiya Lobanovskaya / Pexels

“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

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.

Only Settling For Those Who Were Already Interested

man kisses woman's forehead in a field
Photo Credit: Allef Vincius / Unsplash
Photo Credit: Allef Vincius / Unsplash

“Dating people who were interested in me instead of pursuing people I was interested in. It was so lazy.” – Connie_Damico / Reddit

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.

Giving Players The Time Of Day

woman looks at man as they walk
Photo Credit: Guillan Fremaux / Unsplash
Photo Credit: Guillan Fremaux / Unsplash

“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.”

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.

Living To Please Others

woman praying on bridge with her eyes closed
Photo Credit: Amadeo Valar / Unsplash
Photo Credit: Amadeo Valar / Unsplash

“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.”

“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.

Not Taking The Time To Explore Many Relationships

man kisses woman's cheek as she smiles
Photo Credit: Freestocks / Unsplash
Photo Credit: Freestocks / Unsplash

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

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.

Being The One Hurting Others

couple on date at a restaurant looking sad
Photo Credit: Cottonbro / Pexels
Photo Credit: Cottonbro / Pexels

“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

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.

Lust Is Not The Same As Love

woman holds man's face as they lay under the sheets
Photo Credit: Pixbay / Pexels
Photo Credit: Pixbay / Pexels

“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

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.

Giving Cheaters Second Chances

couple is sad around kitchen table
Photo Credit: Alex Green / Pexels
Photo Credit: Alex Green / Pexels

“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

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.

Always Trying To Seem “Cool”

woman posing with hat and glasses
Photo Credit: Brooke Cagle / Usplash
Photo Credit: Brooke Cagle / Usplash

“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.”

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.

Not Being Honest About Our Needs

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Photo Credit: Cotton Bro / Pexels
Photo Credit: Cotton Bro / Pexels

“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

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.

Believing Words Over Action

two people talk over coffee at the table
Photo Credit: Priscilla du Preez / Unsplash
Photo Credit: Priscilla du Preez / Unsplash

“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

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.

Trying To Fix And Mother Our Partners

woman leans on man's shoulder in a field
Photo Credit: Milan Popovic / Unsplash
Photo Credit: Milan Popovic / Unsplash

“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

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.

Needing A Partner In The First Place

woman looks up at man as he holds her
Photo Credit: Wesner Rodrigues / Pexels
Photo Credit: Wesner Rodrigues / Pexels

“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

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

Not Speaking Up And Standing Up For Ourselves

man and woman stand under umbrella with man holding her
Photo Credit: Shukrat Umarov / Pexels
Photo Credit: Shukrat Umarov / Pexels

“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

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.

Getting Married Before You’re Sure

bride and groom pose for picture
Photo Credit: Vitor Pinto / Unsplash
Photo Credit: Vitor Pinto / Unsplash

“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.”

“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

Feeling Pressured To Always Say Yes

woman with yes on her hand showing it to the camera
Photo Credit: Polina Tankilevitch / Pexels
Photo Credit: Polina Tankilevitch / Pexels

“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.”

“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

Getting Stuck In Codependency

man kisses woman laying on him as she laughs
Photo Credit: Nycolle Suabya / Pexels
Photo Credit: Nycolle Suabya / Pexels

“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

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.

Looking For Someone Who Shared Our Exact Mentality

man and woman press forehead against each other with their eyes closed
Photo Credit: Ba Tik / Pexels
Photo Credit: Ba Tik / Pexels

“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

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.

Not Knowing Our Worth

woman applying red lipstick in mirror reflection
Photo Credit: Sam Lion / Pexels
Photo Credit: Sam Lion / Pexels

“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

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.