I Dated A 20- And A 30-Something Guy, And Neither Of Them Were For Me

by Sheena Sharma

“So, you gonna make me a sandwich or what?"

My ex and I had just done the deed. He held me close, and I lied there unperturbed, trying to soak up the moment, but all I could take in was the smell. His bedroom reeked of sweat, socks and pizza.

Conversations with my ex usually panned out this way. He was 25 and reckless, and I ended it with him because I had enough of his crudity. I'm 25, too, but I find myself straddling the fine line between outgrown reckless and inceptive responsibility.

I left the relationship with one objective and one objective only -- I no longer wanted a boy; I wanted a man.

I didn't know how I'd get there, but I knew I wanted to tread cautiously.

Social experiments have become my new favorite way to spend my time. They're a way to connect with the world without having to commit to any one person and to learn about love from an objective standpoint.

I've reduced dating to a science. The breakup left my heart sore and my ability to trust sour, so removing the possibility of falling in love from the equation entirely seemed like the best option. For now, anyway.

It was time to explore the path to my dream guy. I've often pictured him a little something like this: British, chivalrous, strapping and tall, with the intellect of a man but the vigor of a boy.

So when I pitched my next story idea to my editor -- “A Date With A 20-Something Vs. A Date With A 30-Something” -- I assumed I'd vibe better with the 30-something. After all, it isn't common interests, but common values that sustain a relationship (or so I've been told).

I eagerly jumped into my assignment, making sure to keep my expectations low but my head high. The goal was to find out the commonalities and differences between a 20-something dude and a 30-something dude both looking for love in New York City. So I dated one of each.

My date with a 34-year-old...

Name: Brian *

Where he's from: Born in Manhattan, raised in Staten Island

Occupation: Digital Designer / Independent Business Owner

Description: Brown hair; big, brown eyes; endearingly lanky frame that he totally knew how to style; soft, calm expression that quieted my constantly overdriven mind.

Brian and I met at Brass Monkey, a bar in Manhattan's Meatpacking District. During a night out with my girlfriends, he approached me at a bar and bought me a drink. We exchanged numbers, and he initiated the texting. We briefly texted about our favorite literature to read on rainy days before agreeing to meet up in Madison Square Park.

He was fairly formal in his approach:

I met Brian by a statue in the park. His look was business casual, head-to-toe: He stood at 5'10" in corduroys, loafers and a fitted suede blazer, topped with shoulder pads.

“Should we stay here or go somewhere else?” he asked. “We could do the wine bar around the corner, but I'm not a big drinker, so it's up to you.”

“Here is fine,” I said, alluding to the bench next to us.

We sat down. I didn't mind, to be honest; it was nice to be immersed in nature and away from alcohol for once.

Our conversation piggybacked off our text thread. We spoke of Betty Friedan and Sigmund Freud. He noticed the "love" ring I wear on my left pointer finger, and I told him I'll always believe in it. He noticed me noticing the wispy grays peeking out from underneath his thinning brown hair, and he assured me they were proof of a well-lived adolescence. It was endearing.

There was no denying he was nervous. He had a slight awkwardness -- a certain kind of social ineptitude -- about him. I carried the bulk of the conversation. I suppose I should've figured a man still single at his age would come with a catch.

But he also had an air of complacency about him, an immovable confidence in the way he viewed the world.

“Put down Sylvia Plath,” he told me, “and pick up Ernest Hemingway.”

I appreciate the work of Hemingway -- don't get me wrong -- but I don't appreciate being patronized.

After putting up with being talked down to, my wise companion suggested we take a walk. Why the hell not, I figured. I like walking.

We wandered into a hole-in-the-wall art exhibit. As he analyzed an obscure installment of dirty shoes, I overheard him talking to himself.

“Why are you still single?” I interrupted, not with an agenda, but out of genuine curiosity.

“Dunno,” he admitted. “I guess I haven't been exposed to enough women to make a well-informed decision.”

I couldn't touch his loneliness the way I could gently touch his shoulder. But I could feel his loneliness.

As the evening wound down, so did the date. Keen on giving my lips some lovin', he gave me an innocent peck. I let him.

I sensed he didn't want to waste his time. I sensed he was lost, but he was also looking. In the 34 years he's been alive, he's earned a PhD, cultivated a career he loves and even started a business on the side. He had a strong sense of self, and bad luck in love. But he seemed ready for real companionship -- though I wasn't exactly ready to give it to him.

My date with a 26-year-old

Name: Alex*

Where he's from: Born and raised in Brooklyn, NY

Occupation: Graphic Designer

How we met: Tinder

Description: Caramel-colored skin; dark brown, bordering on the edge of black, hair; sharp, angled features, like a pretty boy with shiny skin who looked like he perpetually has just gotten out of the shower.

After swiping right for each other on Tinder, Alex and I agreed to FaceTime to rule out the possibility that either one of us was a serial killer.

I'd never FaceTimed with a date prior to meeting him in person, but there's a first time for everything. I picked up my ringing iPad to find Alex nestled in bed, clothed in a sweaty gym T-shirt, giving me what I suspected to be his best bedroom eyes.

Homeboy looked like a high, tan Zoolander. He was trying to seduce me, and despite his valiant attempt, he was doing a horrible f*ckboyish job at it.

His roommates might as well have been frozen in time. They comfortably sunk into their couch aside a bong and were staring, mesmerized, at the garish avatars beating each other up on the TV screen. Marijuana smoked filled the corners of my iPad.

It was a dude's dungeon. Memories of my ex came floating back. I secretly wished I could get second-hand stoned.

After shooting the digital sh*t for 45 minutes, he proposed we go out for real-life drinks at a tequila bar in the West Village. Seeing as this date was coming fresh off the heels of my date with the 30-something, I hesitated -- drinks suddenly seemed wholeheartedly half-assed -- but eventually, I obliged.

The next day, I recognized him in his ripped jeans and T-shirt polo as soon as he stepped into the bar. I won't lie to you: I got drunk.

Despite the lack of depth of our conversation -- we covered a range of important topics, from Justin Bieber's peen, to Kim K's questionable assets -- I kind of enjoyed myself. He made me laugh so hard that I almost snorted Labatt out my nose.

When it was time to call it a night, he went in for a kiss on the cheek, and I went in for a hug. We bumped heads, but he succumbed to my arms.

I got home later that evening to a reminder: Alex was just another 20-something trying to get laid.

I doubt his pea-sized brain picked up on my facetiousness. I opted not to respond to his last text.

There were differences in the ways each man carried himself: One was passive, and the other was aggressive. One was clear-headed in life but not in love, and the other was neither clear-headed in life nor in love.

But the most noteworthy difference of all was the presence of alcohol in one date, and the lack of it in the other. It felt paradoxical that I had two completely different options to choose from: the dry and mature date in the park underneath the trees and clean air, or the drunken stupor in a dirty bar followed by jokes about Netflix and chill.

Going on a dry date was refreshing, and I'd like to further explore romance sans vodka sodas, but it's not that simple, because I know I'd miss embracing youth in the form of tequila shots and non-profound conversations.

I'll never speak to either guy again. But if I had my way, I'd take a guy with the 20-something's personality and the 30-something's manners. I'm not ready for a man, but I'm slowly outgrowing the boy.

In the end, though, age is just a number. What it really comes down to is something unconcerned with numbers: I'm not chasing 20-somethings, and I'm not chasing 30-somethings. I'm chasing a feeling.

*Name has been changed.