Several years back, I decided to date a younger man – and by younger I mean 10+ years my junior. Adding to the awkwardness of my could-be-boyfriend choice was the fact that I worked with him.

My friends and I dubbed him “New Kid on the Block” when he first caught my attention. For months, the two of us flirted, he poked and prodded around the dating edges, and I agonized over whether I should give him the signal to proceed.

“I shouldn’t date someone so young.”

“I shouldn’t date someone I work with.”

“I should only date people with whom I think long-term relationships are possible.”

These are just a few of the thoughts that fluttered through my mind as he doggedly pursued me.

While enjoying a lovely dinner with New Kid after work one day, my friend Jennifer’s comments popped into my head.

“Eat the darn cake!” she mocked from the past.

So later that evening, as we said our goodbyes, I let New Kid kiss me.

He asked me afterward why I’d given in, and I recounted my exchange with Jennifer years earlier…

My brain and heart were battling each other about a different guy at the time. Well into a wonderful marriage herself, Jennifer patiently listened as I listed all of the reasons I shouldn’t date the guy under scrutiny, and then she peppered me with questions:

“Sounds like he’s a great guy, yes?”

“Yes.”

“He’s funny, smart, attractive, all of your main criteria, right?”

“Yes.”

“So forget the other stuff, Kim. Just eat the darn cake!”

“Huh?”

That’s when she shared an exchange that she’d had with a 70- or 80-year-old woman (can’t remember exactly) reflecting on her life choices. This wise lady had explained to Jennifer that, as she looked back on her life, she wished that she’d embraced the moment more and been less concerned about all of the ramifications of each choice.

She talked about the countless dinner parties she’d attended in which she passed on the dessert. Instead of agonizing over the calories she’d need to burn off later, which hadn’t made a real difference in her life, she wished she’d dug in and enjoyed every bite.

This woman’s regrets didn’t focus on what she had done but on what she hadn’t been willing to try.

I found this story profound and adjusted my life accordingly.

Somehow, I think my retelling of my earlier epiphany to New Kid got lost in translation.

He found my recounting of it hysterical, and it boosted his ego dramatically. He proceeded to leave me Post-It notes on my desk and sent texts signed “Cake” for months.

What started out as sweet turned sour several fun-filled months later, but thankfully, we remained good friends and colleagues.

I didn’t share the nuances of this relationship with many folks, given how awkward it remains to talk about one’s failed attempts at love, but I think all encounters, pass or fail, should be celebrated.

While the brief romantic exchange with New Kid and I did not result in a long-term relationship, and I flinch occasionally when I look back, I’m glad that I “ate the darn cake” in that instance and many others before and since.

I only hope I’ll have the guts to consume the many slices of life that my 40s will serve me.

(This story was inspired, in part, by WordPress’ Break the Silence Daily Prompt. This post also is one of 30 30-somethings I’m writing for the weekly countdown to my 40th birthday. Celebrate with me as I share other lessons or humbling experiences from the past decade.)

Join me and other writers over at the Yeah Write Weekly Writing Challenge Grid.