How to Fall in Love the Second (or Fifth) Time Around

By Dave Cunningham

January 10, 2024   •   Fact checked by Dumb Little Man

how to love again

We were two mature adults in our mid-60’s, both grandparents, both with divorces behind us. We’d met through a dating website, and this was just our third date, each an innocent daytime picnic or lunch. I saw a spark dance in her eyes and asked, “What are you thinking?” And she startled me with this: “I’m thinking … this is what love feels like.” Huh? How does that happen? And how can you experience that yourself?

It’s Never Too Late

My experience doesn’t just pertain to Baby Boomers. The lessons I painfully learned can be embraced by anybody at any age. I’m sharing my revelations in hopes that you might avoid the kind of heart-breaking mistakes I made throughout my life.

And here is the bottom line, right near the top: Keep an open mind!

I know! That’s so easy, right? Everybody knows that. Sorry, but no, they don’t. Especially males, although females aren’t immune to shallow thinking, either. Here’s what happened to me.

The Problem

to love again

I grew up in Southern California in the Sixties, land of the Beach Boys, sunshine, and millions of blue-eyed blonde girls with beautiful tans and tiny bikinis. Yes, please, I’ll take one of those, and could you throw in pink lips and long eyelashes? What’s not to love?

The problem is, when it came to love, all my choices were based on these parameters, in exactly this order:

  1. Hair color (blonde)
  2. Eye color (blue)
  3. Body shape (voluptuous)
  4. Face shape (roundish)
  5. Content of her character (she likes me)

I was not unusual in this approach, given that it was Southern California and I was young. And I think I can safely say that women at that time and place weren’t all that different, although their desired qualities in a potential mate might vary slightly.

The bottom line (we might have several bottom lines in this story) is that our priorities were all wrong, and it took me 65 years to figure that out. What really matters is the person on the inside … their brain, heart, emotions, likes, dislikes, personality and, most important of all, at least from my point of view, their integrity.

That woman in the first paragraph of this story turned out to be the finest human being I have ever met. And how lucky am I that she loves me?

How the Problem Wreaks Havoc

I’m not happy to be disclosing some of the following, because it doesn’t reflect well on my decision-making, or intelligence, for that matter. But for the reader’s sake, I will admit that I made the same mistake over and over and over again. I added various twists to my mistakes, but they were all basically the same mistake. I chose romantic partners for all the wrong reasons.

My first choice was a woman who loved physical intimacy all the time, anytime, anywhere. Unfortunately, I later learned she also loved it with anybody. My second choice was based on my desire to have a family, so I chose a woman for whom that also was a priority. It seemed like a sound decision, but I realized much later that a healthy couple needs something much stronger to bind them together than just the children.

Rebounding from that divorce, I foolishly went back to my primitive urges and chose a younger, beautiful, and intelligent woman. That blinded me to the obvious fact that she was a diseased alcoholic. And my fourth choice was even more “retro” – a blue-eyed blonde with money. To my great surprise, that didn’t work out either.

The Solution

I would love to tell you that after a series of heartbreaking experiences in romance, I suddenly came to my senses and had an epiphany that led me to finally get it right. I’d also like to say that it’s possible for anyone to find the perfect romantic partner who’s capable of changing your life forever. But those would be lies.

The bottom line (that’s three so far) is that I got lucky. I stumbled upon a perfect woman who doesn’t even know that she is perfect. But I will take credit for one tiny little moment that led me to what now feels like eternal happiness.

This woman and I were exchanging messages on a dating website, and we still hadn’t met. She eventually sent me a photo, and that’s where my lifelong mindsets surfaced once again. After looking at her photo, I responded honestly that she really wasn’t “my type.” I then proceeded to foolishly explain my type as blonde, blue-eyed, and a moon-shaped face (none of which described her).

how to love again online dating

She should have dropped me right there and then. In point of fact, she did write, “I think you’re dumb,” but we continued to write to each other anyway. She later shared that she simply enjoyed writing to me, although she felt (correctly) that I had a lot to learn about women.

Here’s the tiny part I take credit for: When I sensed she was about to permanently sign off, I wrote to tell her that I would like to meet her. I didn’t realize until later that I was at a turning point in my life. My priorities were beginning to shift.

And that led to what has become, truly, the love of my life.

It can happen to you, no matter your age or gender.

The bottom line (yes, that’s number four) is that you need to get out of your own way. Don’t be stuck in a mindset that probably hasn’t changed much since your high school days. Getting to know someone involves far more than swiping right or left or quickly looking at a photo. You might be surprised by what you learn about yourself and the person you are getting to know.

What does love feel like? I just used a bunch of words to scrape away at these amazing feelings deep inside of me, hoping the collective sentences would offer a glimpse, a taste of this epiphany.

But maybe my Lady Love said it best when she told me simply: “Love feels like a warm blanket wrapped all around you.”

Dave Cunningham

Dave is co-author of the newly released book What Love Feels Like: The Dawn of Human 2.0. An award-winning journalist, his work has been published in the Wall Street Journal, Chicago Tribune, Los Angeles Times and many other periodicals worldwide. He also co-authored Travel Within: The 7 Steps to Wisdom and Inner Peace. He hopes the story of What Love Feels Like can help others experience their own epiphany.

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