September 24, 2026 at 12:35 am

He Refused To Hire His Girlfriend’s Struggling Adult Son — Her Disappointment Has Him Second-Guessing Himself

by Benjamin Cottrell

couple agruing man looking tense

Pexels/Reddit

Dating someone with grown kids can put you in some complicated situations.

One business owner found himself in such a situation when his girlfriend of five months asked if he had any job openings for her 20-year-old son, a young man without college plans, steady work, or any direction in life.

He gave her a quick, honest no, explaining he wouldn’t want “someone like that” affiliated with his businesses in any way.

His girlfriend’s visible disappointment caught him off guard, especially since he barely knows her son and doesn’t consider himself any kind of father figure.

He still believes he made the right call, but something about her reaction had him second-guessing his decision.

Keep reading for the full story.

AITAH for not giving my GF’s adult son a job at my company?

I (34M) have been dating my current girlfriend (41F) for about 5 months now.

She has a 20-year-old son that she’s not particularly close with and isn’t super fond of.

However, their relationship has some complexity.

She has certain moments of guilt or regret over the fact that his dad is not in his life and he’s basically meandering through life without a path.

He isn’t in college, doesn’t have a steady job, and seems to have no ambition.

Soon, his girlfriend came to him with a rather uncomfortable proposition.

My girlfriend asked me recently if I had any openings for him at any of the businesses I own.

I could always use good help, but I said I didn’t, because I’d never want someone like him affiliated with my businesses in any way.

My girlfriend seemed sad by the short, direct reply, which in turn made me feel bad.

At the same time, he doesn’t feel like he has any real responsibility for her son.

It’s not like I’m his stepdad or anything. He’s an adult on his own and I barely know him. Just because I’ve been dating his mom for a bit, does that mean I have to try and turn his life around?

I feel like I was in the right, but for some reason that interaction hasn’t sat well with me, and I feel like an AH.

Sounds like he made the decision that was right for his business.

What did Reddit have to say?

Perhaps he’s making a bit too harsh of an initial judgment.

Screenshot 2026 09 18 at 4.05.45 PM He Refused To Hire His Girlfriends Struggling Adult Son — Her Disappointment Has Him Second Guessing Himself

This user speculates on how this son ended up in his state.

Screenshot 2026 09 18 at 4.06.19 PM He Refused To Hire His Girlfriends Struggling Adult Son — Her Disappointment Has Him Second Guessing Himself

This user thinks there’s a fine line between honest and just plain cruel.

Screenshot 2026 09 18 at 4.07.22 PM He Refused To Hire His Girlfriends Struggling Adult Son — Her Disappointment Has Him Second Guessing Himself

He’s really not being very openminded at all about this.

Screenshot 2026 09 18 at 4.08.21 PM He Refused To Hire His Girlfriends Struggling Adult Son — Her Disappointment Has Him Second Guessing Himself

Running a business and running a rescue mission for someone else’s kid are two very different responsibilities, and he’s allowed to keep those separate.

But on the other hand, redditors do have a point. It’s worth asking himself if he actually knows this son well enough to be making these kinds of calls. There’s a real possibility he’s running on assumptions instead of firsthand knowledge.

There’s a difference between protecting your business and writing someone off before you’ve even met them.

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Benjamin Cottrell | Assistant Editor, Internet Culture

Benjamin Cottrell is an Assistant Editor and contributing writer at TwistedSifter, specializing in internet culture, viral social dynamics, and the moral complexities of online communities. He brings a highly analytical, editorial voice to his reporting on workplace conflicts, malicious compliance, and interpersonal drama, with a specific focus on nuanced stories that lack an obvious villain.

As a published author of rhetorical criticism, Benjamin leverages his academic background in human communication to dissect and elevate viral social media threads. Instead of simply summarizing events, he provides readers with balanced, deep-dive commentary into why the internet reacts the way it does. In addition to his cultural reporting, he is an experienced fine art photography essayist and video game reviewer.

When he isn’t analyzing the latest viral debates, Benjamin is usually chipping away at his extensive video game backlog, hunting down the best new restaurants, or out exploring the city with a camera in hand.

Connect with Benjamin on Instagram and read more of his essays on Substack.