no regrets

Yup, I Was The Cliche Divorcee Who Dated A Younger Man

Folks, he didn’t know what Seinfeld was.

Yup, I Was The Cliche Divorcee Who Dated A Younger Man
Ariela Basson/Scary Mommy; Getty Images, Shutterstock
The Divorce Issue

When I got divorced, I knew that the end of my marriage didn’t mean I’d be single and alone forever. Yet I still wanted to take some time to mourn the end of what I once believed was my happily ever after. I went to therapy, spent time with friends and family and tried to figure out what the next chapter of my life would entail. The only rule I set for myself was no dating for a while. At least no serious dating, that is. Which is how I found myself involved with a guy who’d never heard of Monica Lewinsky.

About nine months after my marriage ended, I found myself out for drinks one night with a friend. And after our second — or was that the third? — cocktail, her younger brother and his friends happened to show up. The group included one friend who was so good looking that I audibly gasped when we were introduced. (In hindsight it might have been a hiccup, but still… a hiccup induced by his beautiful face.)

Everyone in the group was being kind to us “old ladies” as her brother kept calling us, but I couldn’t help but notice that Hot Guy (herein referred to as H.G.) paid special attention to me and my needs. He bought me a drink, made sure I always had water and offered to walk me to the bathroom. He was sweet and attentive, not like the boisterous jerks I was used to meeting at bars, and yes, I loved the attention.

There was something different about him; he was genuine when he spoke. Instead of just flirting or saying something generic like “you have nice eyes,” he was specific with his compliments. He told me how my green eyes made me look unique, and that he could tell how much I loved my family from the way I spoke about them, which he thought was such a great quality.

We did the math and learned I was 14 years older than him. 14! I was equal parts horrified and flattered. As the night wound down I could tell he was about to make a move. I was single, drunk and (sort of) old, and this gorgeous younger man wanted to kiss me. I’m not sure what sober me would have done in that moment, but drunk me chose to lean into the moment — and him — and we kissed.

“If I had started my period at 14 years old instead of 15 then I could BE HIS MOTHER!,” I told my friend the next day. She laughed — a lot, actually, but also encouraged me to forget about all of that and just have fun with it. After all, men are always dating much younger women. It would practically be anti-feminist of me not to go out with him at least once.

A few days later we met at a restaurant for our first official date. It was a casual venue and I dressed accordingly, but when I saw H.G. he looked like he had just come from a job interview. Or a meeting with the President of the United States. He was actually wearing a suit, and I’m pretty sure he was also wearing a tie before I arrived because I saw one stuffed in his jacket pocket.

“Did you wear a suit to work today?” I asked.

“No,” he answered, looking at me like I’d just asked the strangest question ever. “Why do you ask?”

I shook my head and stifled the smirk that was unconsciously forming on my face. “No reason,” I told him.

His attire was actually on par with his vibe that night; instead of a casual conversation he seemed intimidated by me. He asked about my career and travels, my life experiences in general, and responded to each with “wow” and “that’s so cool.” It was as if J.Lo was talking with an aspiring J.Lo, he peppered me with questions like I was his mentor and was genuinely impressed — no, dazzled — by my answers.

It was incredibly flattering. And, if I’m being honest, a bit awkward as well. Was he applying for a job or to be my boyfriend?

After that dinner, I felt that our time together had reached a natural end, but H.G. was persistent in asking me out again. Oh, and did I mention what a gorgeous human specimen he was? I tried to make sure he understood that I was only capable of dating very casually at that time and, to my surprise, found myself agreeing to a second date. Maybe I was bored; maybe deep down I actually enjoyed how he seemed to adore me. My ego did take a hit in my divorce, after all.

The cringe factor was much lower the next time I saw him, but our age difference was much more evident. When our waiter described our appetizer as tasting as good as “pure gold” I laughed and quoted a favorite Seinfeld episode: “that’s gold, Jerry!” H.G. looked confused, so I started to give a brief synopsis of the episode until I realized that it wasn’t the scene that stumped him, he’d never heard of Seinfeld at all. Unless we were discussing the weather or what he considered to be my awe-inspiring life experiences, there wasn’t much shared territory we could cover.

When it came to the bedroom, however, we were very compatible. Sex with him was like an intense workout and all the cliches about younger men were true. He was never tired and all he wanted to do was please me. He was my Brad Pitt from Thelma & Louise (a movie he said he was “pretty sure” he had heard of); the opposite of what I’d become accustomed to.

Yes, dating him was a big boost to my self-esteem, and I actually found myself having fun and feeling more like my old self. I was finally ready to leave my divorce in the past and start building my future, though I knew that future didn’t include H.G., handsome and sweet as he was.

Great sex is great, but it’s not enough to sustain a relationship, no matter how casual. After the initial thrill wore off, the awkwardness between us that I was initially able to ignore suddenly felt magnified tenfold. What once felt like adoration was now an annoyance, and being forced to play the role of J.Lo all the time was exhausting. I was ready to just be Jenny From the Block again. And I knew that would never happen with H.G.

When I saw how sad he looked after I told him things were over I almost considered giving it a few more weeks. Until he said that he would never forget the life lessons I taught him and that he hoped to achieve a similar level of success when he was my age. Suddenly I was no longer J.Lo or even Jenny From the Block. I was his college advisor and we’d reached graduation day.

And I was at total peace with my decision.

I don’t regret dating H.G. He was genuine and kind, and I know he truly cared for me. It was exactly what I needed to help transition back into the real world after my divorce. I learned a lot and I think he did, too. Like the time I taught him about using a rewards credit card and earning airline miles, or the benefits of sorting your laundry before washing it. And he reminded me that even in my “older and wiser years,” sex can still be wild and satisfying. And I absolutely deserved that.

Becky Vieira has been wearing mom jeans since 2016. She writes for a variety of parenting outlets, and can often be found oversharing intimate details of her life on Instagram. She's immensely proud of the time she thought to pee in one of her son's diapers while stuck in her car, as opposed to her pants.

Vieira’s debut book: Enough About the Baby: A Brutally Honest Guide to Surviving the First Year of Motherhood is a guide book for women who recognize the necessity of self-care—even if sometimes the rest of the world does not. She lives in the San Francisco Bay Area with her husband, son, dog, three cats and a partridge in a pear tree.