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Having a roommate in your 40’s is weird.

It’s unnatural

By Jesse LeePublished about 2 hours ago Updated about 2 hours ago 3 min read

Having a roommate in your 40s is weird.

He is my best friend of 25 years so when we get together we’re just teenagers with FICO scores.

And they always give us one check at restaurants. Every. Time. 🙄

I have to tell them we’re not together-together and it’s because neither of us is known for doing things that are convenient.

But people are always asking: what’s your deal? I don’t even know how to answer that. It doesn’t have a clean definition. It’s just a “relationship of association because of circumstance”…

… Ok. By pure definition it’s a situationship. 😔

When we were in our early 20s we made a pact that if we were both single in 20 years we’d be together forever. So at least that’s working out. 🙄

When two grown men live together, You find out even little things can bother you. For example, I’ll be binge watching a show in the living room and he will come and sit down and get really into it. When it gets late, I want to go to sleep so I’ll get up and announce I’m going to bed… and this guy says I’m going to watch just one more episode… on my account! Then he falls asleep watching it so three more episodes play while he is sleeping in the chair.

Now my queue is all screwed up and I have to scroll through and try to remember which episode I left off on last night at midnight!

But I got him back 😈.

His YouTube account is logged in on the tv. So when he is working I go on to his account and search: “videos about Furry conventions and glitter crafts”.

Then I wait for when he sits down to watch: “off-road trucker builds” and instead the algorithm spits out: “How to build a man sized sparkly kitten costume.”

I just stare accusingly at him while he panics and scrambles to turn it off.

I make a disgusted face and say: “Maybe you should go as a squirrel?” 🐿️ 😈

This is who I’ve become 🤦🏻‍♂️. I didn’t like it so I decided to do online therapy.

My cousin is always going on and on about his online therapist. He found her on a website called Only Fans? I guess it’s for people that are big fans of therapy or something. 🤷🏻

The woman he sees is a real therapist with a degree but apparently she is paying off her student debts and makes more money seeing clients online. I haven’t checked her out but she must be good because he meets with her all the time. 🤷🏻

I was looking for a male therapist though because a woman once told me I should never have a female therapist. I might accidentally charm her into believing I’m not as messed up as I am.

If I could charm a woman I wouldn’t be doing therapy in my 40’s to get along with my male roommate 🙄.

Ironically the therapist I got paired with loves telling jokes. Like the WHOLE TIME. Also, he is funnier than me which is a nonstarter.

This guy literally looks and acts liked Dick Van Dyke if he was a therapist.

That may sound like fun but imagine Bert from Mary Poppins doing shadow work with you while making fun of your dreams.

🎵 “Chim chimney chim chimney… you are insane”. 🎶

This wasn’t my life plan. I tell myself this is temporary. Having a “roommate” when your hair is already turning gray just feels like the start of a nursing home. That and I’m constantly saying: “I hope my kids come visit me this weekend.” 👴

We’re like “The Golden Girls”.

I think I’m: Blanche. 🤦🏻‍♂️

I’m a delusional love addict that’s always shocked when it blows up in my face.

So I’m taking a break from dating. I know I should get back in the horse but I don’t want to.

Dating in your 40s is awkward. Not just because after being married 20 years my game is gone, if ever I had game. It’s because the last time I dated I was in my 20s. The women were also in their 20s.

I don’t know what women my own age want. If I did I’d probably still be married.

But it turns out women in their 20s like older men because they think we are emotionally stable.

Jokes on you. We’re not.

Also, I have a daughter that’s almost 20 so I know from experience that young women aren’t either.

It doesn’t matter anyways. I’m not ready to date yet.

In the meantime we are just single and supporting each other…

So If you see my roommate and I out please remember that we’re not together… we are just sad.

ComedyWritingFunnyJokesdivorceSarcasmSatireStandupfriendshiphumorsatire

About the Creator

Jesse Lee

Poems and essays about faith, failure, love, and whatever’s still twitching after the dust settles. Dark humor, emotional shrapnel, occasional clarity, always painfully honest.

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Comments (2)

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  • Sara Wilsonabout 2 hours ago

    Lol love this. I was just telling my bestie of 25 years, we need to move in together and be the golden girls. Life goals 💯

  • Rowan Finley about 2 hours ago

    This is hilarious! :D

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