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

So, you gonna build 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 objective it with him because I had enough of his crudity. Im 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 merely — 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 experimentations have become my new favorite way to spend my hour. Theyre a style to connect with the world without having to commit to any one person and to learn about love from an objective standpoint.

Ive reduced dating to a science. The breakup left my heart sore and my they are able to trust sour, so removing the possibility of falling in love from the equation altogether seemed as though the best alternative. For now, anyway.

It was time to explore the path to my dreaming guy. Ive 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 Id vibe better with the 30 -something. After all, it isnt common interests, but common values that sustain a relationship( or so Ive been told ).

I eagerly jumped into my assigning, attaining 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 datewitha 34 -year-old…

Name : Brian* Where hes 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 wholly knew how to style; soft, calm expression that quieted my constantly overdriven mind.

Brian and I met at Brass Monkey, a bar in Manhattans Meatpacking District. During a night out with my girlfriends, he approached me at a bar and bought me a drinking. 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 reasonably formal in his approach 😛 TAGEND

I met Brian by a statue in the park. His look was business casual, head-to-toe: He stood at 510 ” 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 Im not a big drinker, so its up to you.

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

We sat down. I didnt 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 Ill always believe in it. He noticed me noticing the wispy grays peeking out from underneath his thinning brown hair, and he assured me the latter are 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 shouldve 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 — dont get me wrong — but I dont appreciate being patronized.

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

We strayed into a hole-in-the-wall art exhibit. As he investigated 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 havent been exposed to enough women to make a well-informed decision.

I couldnt touch his loneliness the style I could gently touch his shoulder. But I could feel his loneliness.

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

I sensed he didnt want to waste his time. I sensed he was lost, but he was also looking. In the 34 years he’s been alive, hes 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 wasnt precisely ready to give it to him.


My datewitha 26 -year-old

Name : Alex* Where hes 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.

Id never FaceTimed with a date prior to meeting him in person, but theres 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 try, he was doing a horrible f* ckboyish chore 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 beverages at a tequila bar in the West Village. Ensure as this date was coming fresh off the heels of my date with the 30 -something, I hesitated — beverages suddenly seemed wholeheartedly half-assed — but eventually, I obliged.

The next day, I distinguished him in his ripped jeans and T-shirt polo as soon as he stepped into the bar. I wont “re fucking lying to” you: I got drunk.

Despite the lack of depth of our conversation — we encompassed a range of important topics, from Justin Biebers peen, to Kim K’s questionable assets — I kind of enjoyed myself. He constructed 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 ran in for a hug. We bumped heads, but he succumbed to my arms.

I got home afterwards 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 another was neither clear-headed in life nor in love.

But the most noteworthy change 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 matured date in the park underneath the trees and clean air, or the drunken stupor in a dirty bar followed by gags about Netflix and chill.

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

I’ll never speak to either guy again. But if I had my style, I’d take a guy with the 20 -something’s personality and the 30 -something’s manners. I’m not ready for a human, 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: Im not chasing 20 -somethings, and I’m not chasing 30 -somethings. Im chasing a feeling.


* Name has been changed .

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