How to Let Go of Your Dating Mistakes

Men's Dating

How to Let Go of Your Dating Mistakes

Sam Stieler Sam Stieler • 6/12/15

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.