Those who have been fortunate enough to make significant amounts of money should feel no shame in taking care of the less fortunate and should be eager and willing to share the blessings of life with those around them, especially their friends. This question came up in an online discussion we found on Reddit in which a rich man feels awkward when it comes to sharing.

The Original Poster (OP), Good_Culture_628 is a 56-year-old retired man who is married and childless with a net worth of $15 million, a yearly expenditure of $150,000, and a fixed income of $400,000 annually. This is a recent post on r/ChubbyFIRE.

OP likes to vacation, eat out with friends, and isn’t stressed about spending money at all. The problem is all of his friends are in a much lower tax bracket than OP and have started acting weird when OP automatically picks up the check. OP wants to treat his friends but is also concerned about coming across the wrong way.

Key Takeaways

My initial reaction is that I like seeing generous wealthy people. I like that OP wants to just enjoy nice things with his friends. I see nothing wrong with that.

In the discussion, the consensus was that people don’t like feeling undignified, or that they are taking advantage of OP. If OP insists on picking up the tab every single time, it can make people feel inadequate, or that they are in debt to OP (even if OP has never expressed sentiments like this).

Most commenters are saying that he should allow them to pick up the tab every once in a while. OP can pick up the tab when it is more expensive, or an event/meal that he specifically invites his friends to, and allow them to pick up cheaper tabs like lunch dates, or when he suspects his friends might be struggling with money.

One commenter, luckynedpepper-1, says something profound. He said, “Don’t deny someone the pleasure of giving.” Just like OP enjoys being generous, chances are his friends enjoy being generous too. Another commenter, Prestigious_Speech45, said that his dad would often say to his friends, “My dad believed that good friends should always owe each other a dinner, as it’s a great reminder to get together… next time is your turn.”

Another group of commenters suggests that OP should say something like, “I want to go to X. Do you want to come? My treat.” That way there isn’t any awkwardness at all on the day of the activity. More commenters suggest doing cheaper activities and eating at cheaper restaurants. Do activities that are in everyone’s budget, and no one will feel like the relationship is unequal.

One thing that was repeatedly emphasized was to definitely not pull the whole go-to-the-bathroom-and-give-the-waitress-your-card-on-the-way. A surprise “I got it and there’s nothing you can do.” It can be extremely insulting and unnecessary. Most agree that his tactic can backfire in many ways and make friends feel like OP views them as financially inferior.

Another thing that commenters agree to not do is suggest a restaurant that his friends most definitely won’t be able to afford and then not offer to pay the bill. That puts everyone in an uncomfortable situation and can make people feel like you have some kind of superiority complex.

Thank you for reading! Have some feedback for us?
Contact the 24/7 Wall St. editorial team.