People Share 20 Regrets They Have About Past Dating Habits

Memories of past relationships and our former dating life can linger like haunting shadows, leaving a bittersweet ache in our hearts and minds. Regrets serve as echoes of unspoken words, missed chances, and paths we didn’t explore. Frequently, we catch ourselves reflecting on what might have unfolded differently, replaying those moments in our minds akin to a disappointing TV show.

Move Along

One user shared, “When they say they don’t give a f****ck, don’t convince yourself they’ll love you eventually. You just become something to make them feel secure, and you feel like your spirit is dying in the process. Move on.”

Relax

A second user added, “Getting so caught up in the fun early stages of the relationship and planning activities for dates that I forgot to relax and be myself, take it a week at a time and see how things go. Pretty sure it made me seem too pushy, so things didn’t end very well for me. Lesson learned: chill out.”

No One’s Listening

A third user said, “The holy Trinity of bad dating: ⁠Not listening when they told me they weren’t interested. ⁠Not listening when they told me they were crazy. ⁠Not listening to myself when I realized I didn’t want to be with someone anymore. This is the first time I’ve spelled it out for myself like this, and I think I’m seeing a pattern….”

Won’t Go The Distance

This user recalled, “I can’t pinpoint the exact moment or reason behind it, but somewhere in my past relationship, I had a moment where I thought: “This relationship will definitely not be a long-term thing.” That should’ve been the moment when I jumped ship. Unfortunately, I didn’t and got dumped two weeks later because she had to focus on herself.”

Don’t Ignore Red Flags

A Redditor added, “The red flags in month 3 are the same in year 3. I saw things in the beginning that I didn’t like and figured it would take some time to get used to it. It never got better, just worse. Don’t let puppy love cloud your judgment.”

Part Of Who I Am

A poster shared, “I hid some of my hobbies and interests because I was scared they looked dorky. As soon as I stopped hiding it, I met my partner.”

Don’t Settle

A commenter said, “I should not have settled for someone I wasn’t super compatible with just because I was lonely.”

Let It Go

One Redditor commented, “Always being the last to let go and never letting go easy. The never letting go easy is the part I wish I could change.”

Wished I Did More

A top-liked comment said, “I didn’t try to date more in my early 20s. Now I’m in my mid-30s with a combined relationship experience of a little over a year. I basically have the romantic intelligence of a 16-year-old.”

Stop Pursuing

One user said, “I should have stopped pursuing someone when their answer was clear that they don’t like me.”

Living Up To Standards

This Redditor stated, “All I can say is don’t let your sadness be the reason why you failed to live up to the standards and expectations of the person u love/want to pursue.”

Withholding Feelings

A user commented, “I bottled everything up until we had an argument, and I spilled it out all at once, and now we are done.”

Shoot Your Shot

This commenter posted, “Shooting more shots and bringing way more confidence in my 20s. I was a very good-looking guy with very low self-esteem. Funny to look back now at 46.”

Moving For Love

A top-liked comment said, “So far, my biggest regret was moving halfway across the country with someone, and when I struggled to adjust to that location, they refused to move a few hours for me to a different location. That really hurt. Felt like I gave up so much for them, and it turns out they wouldn’t do the same for me. I’ll never move for love again.”

Get Out Now

A user shared, “If someone says they hadn’t spent enough time being single before y’all got together, just break it off so they can do their thing. While it might be hard to give up on something good, the feeling of regret for not getting to experience more opportunities and meet more people will constantly be in the back of their heads.”

Incompatible

One poster recalled, “Letting them get away with bad behaviors. I also tried being overly romantic and giving to someone who didn’t do the same. Lastly, I was overly apologetic even when I didn’t do anything inherently wrong. This allowed them to play victim more often than they should’ve.”

Seeing A Pattern

A commenter added, “I wish I would have never gotten with most of the people I had dated in the past. They were very manipulative and left me with some serious self-esteem issues. It’s kinda hard to get over, and I find it still affects me to this day.”

Stay Broken Up

One user shared, “Taking my ex back after saying no. He left me 3 weeks before our wedding and left me absolutely destroyed for the past five years. Had a mental break, struggled with anxiety, and the worst heartbreak that still pains me to this day.”

Take A Chance

This Redditor said, “Not telling my best friend I were in love with them. ”Protecting our friendship” was really me being a coward.”

Stayed Too Long

Finally, a Redditor said, “I stayed for too long in my relationship. I tried to keep someone who didn’t want to be with me, and all it did was make me resentful and overly cautious in my next few relationships that I eventually ended because I was scared the same thing would happen.”

Source: Reddit

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