I'm worth millions and enjoy picking up the tab when out with friends - how do I make it not awkward?
Briefly

"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."
"Don't deny someone the pleasure of giving." Just like OP enjoys being generous, chances are his friends enjoy being generous too.
Read at 24/7 Wall St.
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