How To Let Go Of Your Dating Mistakes

Men's Dating

How to Let Go of Your Dating Mistakes

Sam Stieler

Written by: Sam Stieler

Sam Stieler

Sam has been writing about dating and relationships for more than three years now. He holds a bachelor's degree from Bucknell University, has self-published a few of his own books and is currently working on mastering the double right turn in his salsa dancing classes.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

Discuss This! Discuss This!
Advertiser Disclosure

It’s a commonly retold biblical story. God told Lot and his wife to flee from their city, warning them to never look back at what the two left behind. Lot’s wife disobeys this command, glances back at the home where she previously invested all of who she was, and found herself promptly turned into a pillar of salt.

Like all good stories, the tale of poor Lot’s wife contains within it a deeply seated truth — looking back at what used to be when you should be looking forward to what lies ahead carries with it some seriously dangerous consequences. And believe it or not, this is doubly true when it comes to how you handle your dating life.

Spending too much time and energy mentally engaged with the “shoulds” and “should-nots” of relationships past may not turn you into a pillar of salt, but it will develop such hardness and crustiness around your heart that the difference between you and Lot’s wife will be slimmer than you may have originally imagined.

Reframing the past.

It’s natural to look back at your presumed dating mistakes and feel a whole lot of regret. It’s natural to allow regret to cloud all of your current attempts at having healthy relationships. It’s natural to feel you will never have the same opportunities as you believed you had in the past, to feel the same emotions you felt in the past.

By and large, these sentiments are true. You really will never have the same exact opportunities you had in the past. You really will never feel quite the same about the new women you meet as you felt about the women you used to be with.

But your past relationships probably aren’t anything worth mourning over.


“The past exists for one reason — to

inform the decisions you make in the present.”

You missed those opportunities for a reason.

First of all, the alleged “opportunities” you missed in the past likely bore little real-world resemblance to how you currently frame them. All of those supposedly “perfect” women you let slip by passed through your life for a reason. Either they weren’t as great as you imagined they were, or they really were great but you weren’t in the right place in your own personal development to match up with them in any deep, lasting manner.

Young love = stupid love.

Secondly, it’s a good thing that you will never fully recapture the romances of your youth. Can you imagine what would happen to your life right now if you fell into the same sort of all-encompassing romance you experienced in your teen years? Your life would completely fall apart and in short order.

One of the gifts and curses of growing older is the fact that we all begin to accumulate all sorts of elements in our lives we don’t want to give up so easily. Not even for the fleeting flame of young, stupid love.

Mistakes are learning opportunities.

The mistakes you’ve made in your dating life can be seen as life-destroying, soul-crushing experiences, or they can be seen as opportunities to learn, grow and become a better relationship partner.

Instead of fretting over the “mistakes” of your dating past, take a cold hard look at why you made those mistakes, whether you’re still likely to make those mistakes, and what you can do to grow from those experiences and prevent yourself from repeating your errors.

There is nothing you can do about the past. The women who “got away” are going to stay away. No amount of mental fixation will change what happened. The past exists for one reason — to inform the decisions you make in the present. So only look back long enough to determine how you can do better today.

Advertiser Disclosure is a free online resource that offers valuable content and comparison services to users. To keep this resource 100% free, we receive compensation from many of the offers listed on the site. Along with key review factors, this compensation may impact how and where products appear across the site (including, for example, the order in which they appear). does not include the entire universe of available offers. Editorial opinions expressed on the site are strictly our own and are not provided, endorsed, or approved by advertisers.

Our Editorial Review Policy

Our site is committed to publishing independent, accurate content guided by strict editorial guidelines. Before articles and reviews are published on our site, they undergo a thorough review process performed by a team of independent editors and subject-matter experts to ensure the content’s accuracy, timeliness, and impartiality. Our editorial team is separate and independent of our site’s advertisers, and the opinions they express on our site are their own. To read more about our team members and their editorial backgrounds, please visit our site’s About page.