Three Women That Make Dating In Your Late Twenties A Spectacular Disappointment


“You’ll be relieved to see this one end. Both for the sake of your sanity, and your suffocated nut sack. Those skinny jeans are fucking brutal, man.”

Dating sucks. For the most part, its one long,endless string of letdowns and rejections lightly peppered with false hope. I, on the other hand, didn’t find out that it sucks a big ole bag of dicks until rather recently. That’s because for the majority of my early and mid-twenties, I didn’t really date.

From age nineteen to twenty three, I waited tables while in an on-again-off-again relationship with a girl who eventually left me to marry a Renaissance fair actor.

And to answer your question: No. At the time I wasn’t aware I had set such an incredibly low bar.

Naturally, that didn’t sit well. So after realizing that no girl wants to date a guy who only shows enough potential to be an assistant manager at Applebee’s, I decided to up the value of my stock. To do that I went back to school to get a degree.

Chicks dig guys with degrees.

Unfortunately, going back to school at a later age meant not getting to date while I was in college either.

From age twenty-four to twenty-seven, instead of focusing on scoring some girls number, I was more focused on finishing school before I was old enough to sleep with a professor without it being weird.

A nineteen year old student and forty year old professor makes the news. A thirty year old student and a forty year old professor doesn’t even make the bathroom wall.

That’s not to say I didn’t date a little. Just nothing meaningful or impactful that gave me a good look into the hopeless, black abyss that dating can be.

After graduating, however, I hit the dating scene with gusto and went on more first dates than Barney Stenson. Sadly, I found it to be nothing like TV. In reality it was just swimming in a dead sea of trite platitudes and uninteresting stories about stupid fucking cats.

For the guy readers who are in a similar situation, let me say it’s not ALL bad. Sure, there will be times where you’ll think if you hear the sentence… “Oh my God, my cat did the funniest thing today”… one more time you’ll slam your face on to the business end of a screwdriver.

But there’s good news…kind of.

In that bland sea of cat stories and uncomfortable laughter there will be three women who will stand out to you. Three women who will actually make an impact. Three women who will give you hope…

…then destroy it a half second later.

1) The Young One:

This one you’ll meet around age twenty-seven. Call it what you will, but everyone knows it’s an attempt to take hold of the last vestige of your youth. You’ll get to the point where you fall asleep at 10pm. You drink white wine because everything else gives you indigestion. You’ll skip a night out with your friends because you planned an early morning trip to Garden Ridge. You’ll be a disgrace to your twenty-two year old self, and you’ll wonder:

 Who is this boring sack of shit I have become?

 You’ll realize that time is slipping out of your hands faster than a toddler out of a parents arms at a gorilla exhibit. You could embrace your age. Come to terms with the fact that you aren’t the finely tuned Porsche that you used to be, but more like a rusty Ford Taurus that smells like stale tacos and farts.

But you won’t accept that because you’re a vain idiot. So instead, you’re going to overreact by getting a tattoo, downloading a shitty Kayne album, and snagging some twenty year old theatre major with a nose ring.

At first she’ll be fun. She’ll take you to all her favorite dance clubs, and keep you out all night. You’ll wake up most mornings wondering where you got a glow necklace and why you’re caked with more glitter than a strippers ass crack.

You’ll be confused when her friends laugh at you when you ask what a Skrillex is, then have to fight the urge to rip your ears off when they play his music for you. But she’ll make you feel twenty-two again so it’ll be worth it, right?


She won’t make you feel twenty-two, she’ll make your feel eighty-two. You’ll realize how hopelessly out of touch with the younger generation you are, and then thank God for it when she makes you try on a pair of skinny jeans.

This one will be over before it even starts. Because deep down you’ll know she’s too young, and despite the sadness that comes with realizing you’re in the twilight of your twenties, you’ll know it’s time to move past those days.

You’ll be relieved to see this one end. Both for the sake of your sanity, and your suffocated nut sack.

Those skinny jeans are fucking brutal, man.

2)The Single Mom

This one will actually have a promising start. By now, you’ll have accepted that youth is transitory. You’ll become more selective in the girls you entertain, and begin to eschew the ones that were too young to remember when Maggie shot Mr. Burns.

You’ll have decided that it’s time to be with someone older and smarter. Someone who has a proven track record when it comes to bearing the load of adult responsibility while remaining down to earth. A woman who can hold an intelligent conversation, but also isn’t so fucking uppity that she can’t see the humor in a good ole fashion Dutch Oven.

 A single mom.

 The first couple of weeks of this relationship will be beautiful. The two of you will hit it off immediately, and you’ll be under the impression it’s because you’re such a great catch.

You’ll be wrong, of course.

Because really, after spending the last three years in a house alone with a tiny human that wears a sack of poo around its waist all day, she probably only agreed to go out with you to get a night off.

But, you’re dumb, so you’ll fool yourself into thinking that it’s genuine, and you’ll actually develop pretty substantial feelings despite the barrage of “insta-dad” jokes from your friends.

Eventually, however, the smokescreen will dissipate, and you’ll get an actual look into the insane cluster-fuck of single mom’s life. You’ll see her sacrifices, and you’ll see her impressive work ethic. Despite being the same age, she’ll make you feel like a kid. Not because of how much you like her, but because of the insane amount of pressure she shoulders without batting an eye. Her selflessness when it comes to her sticky, loud, little roommate will be intimidating and you’ll begin to step away as you slowly realize how woefully inadequate you are for the job shes vetting you for.

In truth, you’ll be woefully inadequate to care for a fucking pet rock let alone help raise someone else’s kid, so in the end this one is probably for the best.

All the same, it’ll sting a little bit. Partly because the relationship was pretty damn good, but mostly because you won’t get to play with her kid’s boss-ass Ninja Turtle toys anymore.

You’ll miss Michelangelo the most.

3) The One You Think Is THE ONE

Then there’s this doozie. The one you thought you were searching for. The one you never thought would happen given your track record of dumpster fires and stage five clingers. The one that will have your head saying:

There’s no way you’re this lucky.

She’ll be a knockout. She’ll be smart. When she stays over she’ll keep you up half the night doubled over in laughter. Even her dick jokes will be funnier than yours.

Every time you’re with her you will have to struggle to center yourself so as not to get completely lost in adoration.

She’ll be the one you do something romantic and spontaneous with on your first date. The kind of shit you only see in a Channing Tatum movie.

…Like sneak on to an empty baseball field in the middle of the night.

You’ll be nervous at first, but despite your trepidation, you’ll find the courage to jump the fence  because when she’s with you there are no consequences.

Hand and hand, the two of you will cut a path through a dark, tepid night redolent of a fresh cut grass and impending rain.

As a joke, you’ll start playing a slow song on your phone. But then, right there on the pitcher’s mound, with her cheek resting on your shoulder, you’ll slow dance.

You won’t notice the cop who miraculously also doesn’t notice the two of you. You won’t notice the sprinklers that go off in the outfield. You won’t even notice the pain in your face from smiling so much.

Because in between the swims you’ll take in her matchless, honey brown eyes, you’ll be officiating a fight between your heart and your head. A fight your head always used to win.

 Used to.

This time things will be different. This time, despite the pleas from your head to be logical, your heart will already be gone.

Lost in her scent.
Lost in her eyes.
Lost in that dance on a pitcher’s mound in the middle of the night.

All your head will be able to do is wearily concede to what your heart will find out the second she stands up on her toes and presses her lips against yours.

That she’s the one.

Unfortunately, your head’s prognostication from the get-go will be right. It will know way before your heart succumbs that you really aren’t that lucky. It’ll know there’s no way she feels the same way about you.

And she won’t. Not even fucking close.

Maybe she just won’t be that in to you.
Maybe she’ll be using you as leverage to get back with an ex.
Maybe she’ll get convicted of murder and disappear to Mexico to run a brothel under the fake name of Mama Sweets.
Maybe she’s actually a guy.

It could be any number of reasons. But you won’t really know why, and you never will. Because after her, you fucking give up.

She’ll be the one you’ll fall for who won’t fall back. She’ll be the final straw that forces you to step back, look at the dating scene as a whole, give it a big fucking middle finger, and say:

Fuck. This.

You’ll decide to hang em’ up until you’re thirty, and you will hope against all hope that dating in your thirties is better than the hot, steaming pile of putrid disappointment that is dating in your late twenties.

I mean, It can’t get worse, right?


Written by Daniel Oliver

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