"Paycheck to Paycheck" Boss Wants to Buy Expensive Dinner

[MrStash2000]

I currently work with a guy who has a wife and two kids and lives paycheck to paycheck. He is a great guy but you know the story: he has the usual two brand new 2015 luxury SUVs and pretty much keeps up with the Joneses. He of course doesn't even get that he is broke. Anyway, he wants to take me and my wife out to a four-star expensive steakhouse. Typically, I would just take the free fancy-pants dinner and run BUT he has two young kids. His situation is so bad that we have to wait until the end of the month for him to get paid. I've already tried to suggest a cheaper alternative and got shot down.

So - do I just take the gift or GENTLY facepunch the situation straight? Suggestions?

[Syonyk]

His decisions aren't yours to make or judge on.  Maybe he's got some sort of inheritance or something going on you don't know about.

And I do like a good steak.

I'd take the offer.  *shrug*

[La Bibliotecaria Feroz]

This is a tough one because he's your boss. I would also feel really icky about it, but I don't see a good way out for you.

You could reciprocate by inviting them to your house to show how good at-home dining can be :-).

[Eric]

Will declining this offer will be a light bulb moment for him where he decides to take the money and set up a college fund?  If not, enjoy your steak!

[FatCat]

Do you know he's living paycheck to paycheck? Some people who are doing very well will act like they're living paycheck to paycheck just to avoid jealousy.

You made the offer for a cheaper alternative and he rejected that offer. I would go to the restaurant. If you don't go to the restaurant with him, he'll just blow money on some other frivolous thing. And rejecting his offer on the grounds that you feel he shouldn't be spending that much money on restaurants will make him feel judged and annoyed.

[kewper]

I agree with the above.  My thought is that this doesn't sound like someone I'd want to work for, if his financial situation is that bad. I'd look for a new job.

[MrStash2000]

Thank you for responses. I kinda dig the one where take it but offer to have them over for a dine in experience.

For those asking how do I know about his finances? Trust me, I know.

[RangerOne]

As someone else said you rarely know the full scope of someones finances. He may have safety nets that have always let him feel comfortable burning his paychecks. Who knows.

I wouldn't refuse a dinner offer over feeling bad about that. I might refuse free dinners at a restaurant I wouldn't be comfortable paying for myself. It would depend on the friend and the occasion.

[mjb]

Another vote for just going. So long as there's no expectation of reciprocation: it's a gift, accept it graciously.

I got to eat a Noma in Copenhagen when the band I work for swung a last-minute reservation. I wouldn't have paid $500 out of my own pocket to eat there, but I sure as hell wasn't going to give up the opportunity if they were going to pay for it!

[The_path_less_taken]

I understand why people are saying take the steak.

What I don't get is why your boss is asking you out like this? It's a company thing or he just likes you or???

He's grooming you for his job?

I guess, since I am bereft of tact, I personally wouldn't be able to go without thinking of his kids and probably saying something stupid that would piss him off and force me to look for a new job.

So the people who say "have him over to yours to pay him back" are probably right. That way he can see that fun is time spent, not money pissed away.

[okits]

I guess, since I am bereft of tact, I personally wouldn't be able to go without thinking of his kids and probably saying something stupid that would piss him off and force me to look for a new job.

LMAO.

OP - go and enjoy.  I assume he's taking you as some kind of gift or thanks for a job well done.  Consider it part of your compensation and/or part of his managerial style.

He's your boss.  Tread very, very carefully if doing anything that resembles correcting or discouraging his spending habits.  He has hire/fire power over you, but not vice versa.

As for his kids, he may be inadvertently teaching them that they don't want to be paycheck-to-paycheck when they are adults.  One dinner doesn't take the roof out from over their heads or ruin your boss's retirement (the accumulated effect of his years of choices may do that.)

[Ricky]

Unless you have the password to his brokerage and bank accounts, I'm not sure how there is anyway to know this besides him being under oath and admitting it.

Either way, his finances are not your concern. There's no good way to bring up "you need to get your shit together before buying other people things". Even if you can't go through with it in good conscience, I would still do it as there really isn't a good way out. Broke are not, it's something he wants to do. It's like declining any gift: you're more offensive by declining.

[Exflyboy]

Agreed.. He's poor because he does dumb shit with money.. Now he wants to do more dumb shit with money.. not your concern.

Besides which he thinks somehow he owes you this.. so take it, its pretty simple and there is no good way to correct him.

You can't save the world my friend..

[HazelStone]

Accept graciously. Order on the cheaper side of things. And one glass of wine at most, if you drink.