Postgrad Dating Nightmares



As I’m sure you’re all painfully aware, what it means to be single changes drastically the moment you walk across the stage to receive your diploma. While you may have escaped without being “that” person who got married to their college sweetheart, you’ve also left the single most convenient place you could ever go to meet potential suitors that are driven, attractive, and approximately the same age as you. Shit. So now what? Well, you have a slew of dating options. Too bad most of them turn into nightmare scenarios. Let me share from experience which postgrad dating nightmares to avoid, and why.

The Tinder Date

The struggle is real for those of us too old to meet new people through real-life social interaction, but too young to resign ourselves to online dating. Enter Tinder. At first, this app seemed like the savior for attractive twenty-somethings looking for potential dates…until I went on my first Tinder date with someone I can only describe as a “postgrad try-hard.” I jokingly mentioned ordering a Natty Light at happy hour as a throwback to my college days, when Mr. Tinder gave me a condescending look and started telling me about the time his mom moved him into his “frat castle” while he pounded Natty Lights in front of her and made her unpack his boxes while he went to a rager.

In his continued efforts to charm me, Mr. Tinder also mentioned how in his two years as president of his fraternity, one of his brother’s girlfriends posed nude for Playboy, mentioning in her bio that she was a sweetheart of that fraternity. He giddily told me how all of the guys in their chapter received signed copies, and how he still values his to this day. I really thought it wasn’t going to get any worse until he proceeded to tell me about his “sick new place” – the apartment building right across from the undergraduate campus.

This is just one example of a Tinder date gone wrong, but after reading some interesting pick-up lines (“Wanna go on a ate? You’ll get the d later”), it’s safe to say I’ll be steering clear of Tinder in the future.

The Young “Political Affiliation” Date

In our postgrad panic to get connected and meet new people (future spouses), my friends and I decided to sign up for our local Young Republicans group. What a joke that was. During my very brief stint as a Young Republican, I was set up on dates with a guy sporting a pair of Superman socks as well as a “local celebrity.” It was made abundantly clear to me on both of these dates that they were very, very, VERY important individuals, and I was lucky to have a minute of their time.

Mr. Superman Socks believed himself to be somewhat of a political big-wig, and clearly whatever I occupied your mind with was substandard to the lofty ideas of government parading through his head 24/7. Mr. Local Celebrity, on the other hand, was part of the group to make connections with people that mattered, and if you didn’t have the means to fluff his ego, he didn’t have the means to buy you dinner.

As someone with a college degree, I am attracted to smart, motivated men. However, I learned not to waste my time on someone who didn’t have a second of his to waste on me. Which brings me to….

The Friend from College

Meeting new people as a postgrad is hard. It can be tempting when you’re completely out of options to run through potential dating scenarios with that guy or girl you’d always considered dating in undergrad but had never actually made a move on them…until you actually do.

I recently got involved with someone exactly like this. I’d been relatively close with this guy, “Cody,” for the majority of my time in undergrad, but neither of us had ever dated the other. It wasn’t until we ran into each other shortly after graduation that sparks began to fly and we ended up on our first date. It seemed like dating Cody would be the answer to all of my problems – we had the same education, the same sense of humor, had seen each other through breakups, and knew each other’s drink of choice. That is, until we started to realize why we never dated in the first place.

He wanted a housewife. I wanted to go to law school. He wanted to live in the country. I wanted to live in a city with connections. He wanted someone to listen to him talk continuously about his life, and so did I. Eventually we became so frustrated with each other that even when we broke things off and decided to stay friends, we didn’t talk for months afterwards, and that was only a short text to “check in” and then not-so-subtlety inform the other one of our updated relationship statuses.

The fact of that matter is that there’s probably a reason you spent four years in close proximity with this person without ever feeling the urge to date him or her. It’s easy to put on those graduation goggles, especially around people of the opposite gender, but trust me when I say that the only thing that will make your ten-year-reunion even MORE awkward is when the ratio of old friends you’ve seen naked increases exponentially.

The Random

After several failed attempts at dates with old friends or people with whom I shared common interests, it seemed like a great idea to date someone I’d never met before. Enter the random. I went in for what I thought would be a quick trip to the Apple store, and left with a smile on my face and a phone number from an attractive businessman. What could go wrong? As it turns out, quite a bit.

After a few flirty texts, I was asked to a nice dinner at an upscale jazz restaurant downtown. Finally, exactly what a postgrad date should look like. I dressed for the occasion in a little black dress and pumps. My date, who clearly missed the memo, showed up in a band tee with a flat-billed hat. “It’s ok,” I thought to myself, “I can change a wardrobe, and besides, he’s been at work all day.” If his outfit was the worst thing about him, I could overlook that small detail.

It wasn’t the worst thing about him. I spent a painfully long dinner listening to him berate the idea of getting into debt over a piece of paper, and that clearly anyone who had any sense could see that that was a stupid idea. Since my date and I rode together, I didn’t really have the option to turn down part two of our fancy night out, which included grinding at a dirty bar, taking shots “as long as they were under $3,” being forced to smoke hookah, and having my palm read. I knew I was done with this date even before I walked outside, and Mr. Flat-billed Hat proceeded to lick his finger and rub the mascara off of my face.

The Set-Up

At first this seems like a great idea. Then the date happens, and you realize this couldn’t actually be much worse. Since you two met through a mutual friend and not college, work, an activity group, or literally anything you could possibly have in common, you’re in for a painfully awkward evening that will probably go something like this:

“So, you know Martha?”
“Yeah, she’s great. She does a wonderful job in accounting. How did you meet?”
“Oh, she’s just an old family friend.”
“That’s nice.”
“So….lovely weather we’re having.”

With nothing in common to talk about, you’re in for a painfully awkward evening that could have been avoided with a “Thanks, but no thanks” to being set up with someone you know nothing about. That’s not to say you can’t have a great 8 hours with someone you bring home from the bar, but if drinking (or Martha from accounting) is your only common interest, it’s probably safe to say that those 3 hours could be better spent on Pinterest, doing your laundry, or catching up on sleep.

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Steph W.

Steph W. is a new Master's degree graduate with an intern's salary and six-figure taste. She realizes her expectations far exceed reality, so she spends her days pinning away Loubs she pretends are in her physical closet instead of her virtual one. Her hobbies include attempting to trapping her boyfriend into marriage before he finds out how insane she is and pretending that Black Box wine tastes as good as the kind she could afford when she was gainfully employed. Send her tips for getting out of student debt at

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