Running a small company can blur the lines between friendship and business, but this boss may have crossed a line without even realizing it.

After regularly letting his employee pick up the check at lunch and only expensing his own, his girlfriend’s reaction has him questioning if he’s being fair—or just taking advantage.

Read the story for all the details!

AITA for letting my employee pick up the check

I run a small company. One of my friends works for me and has a senior position (as senior as you can be at a small company).

He and I go to lunch regularly. Sometimes he picks up the check, sometimes I do.

We always end up talking about business for a good chunk of lunch, though we are personal friends as well.

What a nice combo.

Today I asked the server for the itemized receipt so I could expense the lunch. My friend/employee asked, “you expense these?”

I told my girlfriend this story and she reacted very negatively.

She said I should either pick up the check every time and expense, instruct my employee to expense when he picks it up, or neither of us should expense every time.

Oh boy. Now the line is blurred.

She thinks it is unfair for him to pay out of pocket and me to pay with the company’s money.

As a founder of the company I think it’s perfectly reasonable of me to use my discretion about when a lunch can be expensed, and I’m not doing anything wrong by letting my friend/colleague pick up the tab.

AITA for letting him pick up the tab, and expensing it when I pick it up?

When you’re the boss, every decision carries weight—even who picks up the lunch tab.

But when personal relationships mix with professional expenses, is it just discretion, or is someone being unfairly treated?

It’s definitely that this boss is a big ‘ol you-know-what.

This person made a heck of a point.

And this person think there will be consequences.

Blurring the lines between boss and buddy is all fun and games—until the check comes.

This guy had to know he was wrong.

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