Over the years, it’s easy to develop a lot of dating regrets. If you’re an introvert like me who tends to think deeply about things, these regrets may weigh heavily on your mind and heart.

Here are some of the most common dating regrets:

The one that got away

You may think longingly about a love lost. It’s hard to let go because this person seemed perfect for you—at least that’s what you wanted to believe.

Memories play on repeat in your mind, as if thinking about it hard enough will heal the past. You constantly wonder what you could’ve done differently to make things work and it’s exhausting!

The bad relationship you tried too hard to fix

Have you ever stuck it out way too long in a relationship that was destined to fail? You thought that things would get better, but they only got worse.

If you hung on for too long, you may regret all the time you wasted on a relationship that ultimately failed. If only you’d listened to your gut and called it quits earlier.

The harsh words you wish you could take back

Relationships can get messy. Many of us have said hurtful things that we regret. You may find it harder to let go of the pain you caused another than the pain they caused you.

If only you could go back in time and take back those harsh words. You’d be kinder, more thoughtful and less critical.

The words you left unsaid

Sometimes, it’s the things we don’t say that really haunt us—especially for introverts.

Maybe you didn’t express your feelings as much as you could have. Or you didn’t tell the person how much you appreciate them until it was too late.

These are just a few of the relationship and dating regrets you might be harboring.

It’s painful to hold onto the regrets of love lost—or love that never had the chance to truly blossom.

You might wish with all your heart that things could’ve been different. Worse still, you wish that YOU could’ve been different.

You wonder how the outcome might’ve changed had you been able to say or do the right things.

But choosing to torture yourself with these kinds of thoughts serves no purpose. Deep down you know that the regret is holding you back from opening up to something new.

If you’ve been clinging to the past, here are some tips to let go.

How to Let Go of Dating Regrets

Identify the lesson

What was the gift or lesson that you gained from the experience? And what would you do differently next time?

The most painful lessons can be the most valuable. They bring to light love blocks that you could’ve spent a lifetime ignoring: insecurities, fears, limiting beliefs, emotional triggers.

Choose the happier belief

Your love story may have lots of unanswered questions. Did they really love you or were they just pretending? Did it end because the relationship had run its course or was there someone else?

If you can’t know for sure, you might as well choose what to believe. For example, you can choose to believe that it ended because you’re unlovable…

Or you can choose to believe that you really weren’t right for each other and there’s someone more suitable out there for you.

Provide your own closure

It’s often impossible to get closure from another person. You have to provide it for yourself. There are a few ways you can do this.

Write a letter expressing your feelings. Whether you send it or not, you will feel a sense of peace knowing that you got things off your chest.

You can also set a date to stop thinking about the person and move on. You might even mark the occasion by doing a burning or balloon release ceremony that symbolizes you letting go.

Open up to new possibilities

Holding onto regrets closes your heart to other possibilities. It’s important to choose to open up to something new, because here’s the thing…

There are ALWAYS fresh opportunities to find love—especially when you release the baggage and keep the wisdom. When YOU change, so will your dating experiences.

Just look at my client, Travis. When he came to me he had a painful pattern of attracting toxic women.

After using my introvert framework for attracting great women, that started to change very quickly. Within months he’d met his now-wife.

He explains:

“By the third month I had women coming into my life who were what I considered to be ideal. Michaela also gave me excellent practical coaching with regard to dating. Everything from conversation starters to style advice. I actually met N in late January, 2020 and we dated all through the pandemic and got married in 2021.”

Imagine what’s possible for you! Your love life could completely transform with a few simple steps:

  • Let go of past regrets.
  • Develop a confident dating mindset.
  • Master practical conversation, flirting and connection skills.

I share all of the above and more in my 1:1 Dating Coaching Program for Introverted Men. Click below to learn more and book a complimentary Dating Strategy Session.

Learn More About Dating Coaching for Introverted Men

It is possible to let go of the past and find lasting love. I’d love to be your guide toward building dating confidence and attracting your ideal partner.