Dating A Twenty-Something When You’re 30 Something

First published in the Santa Barbara Sentinel under the pen name, Elizabeth Rose.

My friend and I took a moment to survey the scene.

The dance floor was packed with women dressed in ruffled skirts and lace and men in festive ranchero attire.

It was Celebración de Los Dignatarios at the Santa Barbara Zoo and the crowd was beginning to get a little tipsy – you could tell by the way people raged to the band’s makeshift version of The Commodores’s “Brick House”.

I obviously needed to catch up.

Before making rounds to the wine and food tents, a visit to the ladies room was in order.

I wandered over to the nearest vendor for directions.

“Hi! Where’s the restroom?” I asked the guy manning the table.

“It’s right behind us,” he said, hooking his thumb over his shoulder.

“But you can cut through the booth if you’d like.”

It took a second for me to register his cuteness. His dark brown hair, creamy skin, and bright blue eyes made my head cock in approval.

“Thanks,” I said, giving him my best flirty smile.

I walked away, making a mental note to stop by on my way back to the party.

After answering the call of nature, I washed my hands then stood in front of the mirror to check my makeup.

A minute later, my friend joined me.

“He’s a cutie!” I said as I applied a coat of lip-gloss.

“Yeah, he’s cute but isn’t he a little young for you?”

I shot her a side glance.

True, he was more in her age range than mine (she’s about six years younger than me) but my vow to be open-minded in my single life included older and younger men.

Twenty-somethings need apply.

“Age ain’t nothin’ but a number,” I said.

So much for my wingwoman.

As we walked back to the party, my friend spotted a familiar face and ran off saying we’d find each other on the dance floor.


I could use a break from her negativity plus I had a little errand to run.

I spotted Cutie refilling glasses and talking to drunk patrons storming the tent for refills.

Holding back, I gained a little liquid courage with wine samples at another table.

As soon as he was free, I walked over.

He looked up just as I entered the booth and a big smile lit up his face.

“I’m so glad you’re back!” he said.

After a minute of casual pleasantries about the party (nice set-up), the sunset (so Santa Barbara), and the vintage leather fringe skirt I was wearing (thanks for noticing), he asked for my number – which I happily scribbled down on a cocktail napkin.

He called the next day to plan our date.

The following week at The Good Lion over a champagne cocktail for me and a bourbon for him, we sniffed each other out.

I learned he grew up on a 40-foot sailboat in the harbor and was home-schooled by his parents.

“Yeah, it’s a little odd to have grown up on a sailboat, but I could play my drums as late as I wanted and no one was around to hear me!”

He was charming, polite, and engaging.

I flirted a little more to secure a second date.

He told me about his new place in Ventura, a house he shared with two roommates he didn’t really like.

“But the best part is the view from my bedroom!”

He pulled out his phone to show me a picture and I gasped.

He was right, the view of the ocean was pretty stunning, but the view of his room was not.

T-shirts, socks, empty soda bottles, and papers strewn the floor, and what I could only guess was dirty laundry hanging off a broken pedestal fan.

The cherry on top was his dog was in the corner with a shoe in its mouth.

At that moment, I realized he may not be too young for me (okay, maybe a little), but I was definitely too old for this.

We ended the date with a hug and he promised to call the next day.

The following day, he did call.

And I, shamefully, forgot to call him back.

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  1. I could probably ignore it for a few more dates. I’m not the neatest, but I also have zero space. He sounds Sweet and polite. 2 amazing qualities

    • Very true, way to look at the positives! And I hear you on the neatness but when it’s your mess, is it really a mess? 🙂 Also, me judging him says more about me than it does him. As if I am projecting the “dirty laundry” I needed to clean in my own life. Whoa…deep. Thank you for reading, Katie, and sharing your thoughts!