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A few years ago at a conference I was all but certain I was about to get fired so I refused to spend too much money eating out. My co-worker paid the entire bill at a steakhouse for us to eat dinner at (~$200). Needless to say, I was quite grateful.

I never did get fired and I'm in a much better place now. My co-worker is coming to visit my city (we're all remote around the country now) and we're going to meet up to eat.

Should I cover the entire bill to pay back the dinner he bought me a few years ago? Or am I being weird to bring up something that happened a long time ago?

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    How is this about the workplace and why would be paying off the favor weird?
    – LoremIpsum
    Nov 26, 2023 at 16:52
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    @LoremIpsum socializing with coworkers is part of the "workplace" for the purposes of this site. The dinner wasn't a "favor" it was just paying for dinner. There is a lot of subjectivity in if, how, and when something like that should be "paid back."
    – user175183
    Nov 26, 2023 at 17:11
  • If you're travelling for work, doesn't the company pay for meals? Are you talking about putting it on your expense report this time? Nov 27, 2023 at 16:38
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    @thursdaysgeek the company gives us like $75 a day for meals since the conference covers lunch and breakfast. We kind of have high taste that will go way beyond the $75 hence the need to pay.
    – user175183
    Nov 28, 2023 at 22:11

2 Answers 2

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Seems perfectly reasonable to say 'You got it last time, you're in my town, so time for some insert name of area hospitality - my treat'

It's only as weird as you want to make it.

a $200 meal for 2 is nothing to be weird about at a Steakhouse, it's not like you are going through several vintage bottles of Champagne.

The only question though, which I suspect may be a factor, is if you and the other person are opposite genders and you are worried that it might be perceived as a 'date' or an attempt to hit on your co-worker. In which case - just be clear it's you reciprocating the same hospitality that they showed last time you were at a business function together.

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    Thanks. This was my hunch. And it's a same-sex co-worker.
    – user175183
    Nov 26, 2023 at 19:59
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    In that case - definitely don't worry about it. Nov 26, 2023 at 20:01
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    @TheDemonLord umm .. you may not have heard this where you are, but there's this thing nowadays called "same sex relationships". And gasp, people in them go on dates and hit on each other.
    – Peter M
    Nov 27, 2023 at 14:48
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    @PeterM - Sure - but in terms of Office and Workplace reputation - Two Men going to Dinner and two Ladies going to dinner will never raise the same sort of Eyebrows as a Man and a Lady going to dinner. Nov 27, 2023 at 19:03
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    @TheDemonLord despite the obligatory "peanut gallery" comment(s) this is a great answer.
    – Pete B.
    Nov 28, 2023 at 13:34
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You remember this incident fondly, yes? Handing the coworker some cash and saying "there, we're even now" would be weird. But telling them "I still remember you taking care of my dinner back in 2019, it meant a lot, please let me treat you to a really nice dinner on this trip" is not weird. It's heartfelt.

Now, it's possible it meant almost nothing to your co-worker, who barely noticed, so don't make a big thing of it, but for sure a chance to say thankyou and to be generous is a chance you shouldn't miss. And I expect it will be an enjoyable evening.

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    This, the mere fact you remembered a good deed from that long ago and want to pay it back would be an excellent feeling for most people. It is ALWAYS worth making someones day!
    – Kilisi
    Dec 4, 2023 at 21:11

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