Second Chance: Fresh Opportunity or Waste of Time?

Keeping an Open Mind While Avoiding Old Mistakes

Bonnie Barton
P.S. I Love You
5 min readJul 14, 2018

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Credit: stocksnap at Pixabay.com

I’ve had poor timing with several guys. When we have parted ways, I have found myself wondering if I will ever hear from them again.

From my experience, it’s ill-advised to hold your breath for someone to re-emerge. They rarely do.

But!

To my shock, I had TWO guys circle back around earlier this year.

The timing was out-of-a-movie for the first one. The “friends first” guy from this story reached out to me the EXACT SAME NIGHT that I had the awkward conversation calling out the guy from this story:

What were the odds?!?

Friends first guy (I’ll call him “George”) and I hadn’t been in contact at all in almost two years. There was no animosity between us, but we mutually ended it and drifted away.

Two hours after hanging up with the guy who wanted to use me, I received a message on Match from George. Honestly, my assumption was: “Geez. I already went out with him and he’s already forgotten me.”

That happens from time-to-time, so it wasn’t a bizarre assumption on my part.

I was very pleasantly surprised when I read his message, which was friendly and made it clear that he knew it was me.

He asked to call me and I agreed. Why not? My night couldn’t possibly get any worse!

He was a sweetheart. We swapped dating nightmares and commiserated.

I was floored when he point blank said: “Bonnie, you are by far the best person I dated in the past two years. I regret that I didn’t try harder to make it work with you. I’ve been wanting to tell you that for months now.”

He continued: “That’s why I wanted to reach out to you. Will you give me another chance? I want to take you out. I want a second chance with you.”

I paused for a moment and responded: “Oh, my goodness. Your timing couldn’t be any better. I have had a lousy night. Thank you! But in my mind, you and I closed the door and I don’t want to re-open it.”

He was incredibly gracious: “Wow. That only makes me like you more, Bonnie. Thanks for the direct response. I understand.”

I reiterated my gratitude, wished him all the best, and made it clear he was welcome to reach out in the future to swap stories or for a sympathetic ear.

For those who read the story about George, you know that it was simply too confusing and the chemistry was lacking. There was no need to re-visit this relationship. I knew 100% how I felt.

But what a surprise and a compliment! What a gift and a blessing!

I don’t know how many of you out there have been given a chance like that, but it has been very rare for me.

A little over a year ago, I met someone who captured my heart. And I believe he felt the same way about me.

I will simply say that he was not in a place to be in a relationship with me. Or anyone.

I was crushed. Devastated.

In my smallest, quietest voice: Yes, I was heartbroken.

I picked up the pieces and moved on. There was nothing else to be done.

For months and months there was no word from him.

Then suddenly he reappeared three months ago.

I got some healing, understanding, and closure.

But whether he meant to or not, his contacting me kicked the door to my heart wide open again.

I was cautious, but decided it was worthwhile to spend some time with him once more. We quickly realized that we were as enraptured with each other as ever.

There was no doubt in my mind that a gift had been handed to me and it was worth exploring…just in case enough had changed to make a relationship feasible.

In the end, he is still not in a position to be in a relationship with anyone.

My heart breaks again. But maybe it hurts less because the cracks were already there.

Maybe I was expecting it.

Maybe I was prepared for it this time.

Regardless, I have to face the reality of the situation.

And I don’t do delusional for very long.

So I shrug my shoulders as I cry.

My pragmatism wins every time.

I’m trying to focus on some of the clarity I received from him rather than the disappointment and emptiness I feel at losing the rare person who has felt like “my person.”

I’ve had other second (and third) chances when I was younger, but since I began dating after my divorce it has been unusual to find myself in a position of re-visiting relationships with guys from my past.

I don’t think I have a solid rule when this occasional opportunity presents itself. I’m going to take the stance that I will evaluate them on a case-by-case basis.

If someone special circles back around, I plan on remaining open to seeing where they are now and whether it makes sense to explore a relationship again.

Balance remains paramount: Straddling the line of being open to possibilities while avoiding repeating mistakes.

I am compelled to add: Writing here in Medium has helped me in evaluating this latest relationship opportunity. I find myself looking to my own words! I thank y’all for reading and sharing your stories. It’s been a symbiotic relationship for me and I feel a certain amount of increasing accountability as I approach my own dating experiences: Would I want one of my readers, friends, or followers to be in this relationship? It provides guidance. An unexpected but happy by-product of writing here! But letting him go is especially difficult. He was one of the special ones. Sigh.

Bonnie was off the dating market from 1998 (when she met her now ex-husband) till early 2014. She has been online dating on-and-off for over 4 years. She has gone out on at least 100 first dates, interacted with over 1000 guys, and reviewed at least 10000 profiles. If there was a Masters in Online Dating, Bonnie’s earned it. This means: (1) That Bonnie is a failure at dating AND (2) She’s accumulated a lot of experiences and knowledge about the dating landscape for middle-aged chicks in Austin.

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Bonnie Barton
P.S. I Love You

Queen of mixtapes. Lover of music, travel, and fashion. Authentic sharer of life lessons and dating foibles.