I Was OK Subsidizing My Cheap Friend. But Then He Dropped a Bomb on Me.
Briefly

The article discusses a user's dilemma about a friend's stinginess with shared expenses, only to discover later that he's an heir to a significant fortune. Despite his vast wealth, the friend exhibits behaviors of financial frugality that confuse mutual friends, leading to a deeper inquiry about one's perceptions of wealth and financial responsibility. The advice focuses on confronting these payment discrepancies openly, using tools like Venmo for clarity about amounts owed, possibly revealing underlying issues with financial awareness or psychological behavior toward money.
"One is that your friend is simply very bad at math. Venmo has a function for managing the mathematically inept, allowing you to request payment directly."
"Another possibility is that your friend has family money coming but is not benefiting from it at the moment. It's not uncommon for those in financial security to act frugally in public."
Read at Slate Magazine
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