Our first caller is a 28-year-old single woman living in Chicago — we're calling her Clarisse — who makes $90,900 a year. She wrote a Money Diary last summer where she chronicled her dating life, which included screening texts from her toxic ex, hooking up with a new guy while keeping up with her FWB (friends with benefits), and complaining about how expensive dating is. But what piqued our interest was a conversation she had with her date, G., about the protocol around who should pick up the bill on dates. They agreed to go 50/50, but commenters were quick to point out that Clarisse let G. pick up the tab more (nothing gets past the MD commenters!). We wanted to hear an update from her on how her love life is going, what it's like to date men who make less than her, and how do you actually handle that first-date awkwardness over who should foot the bill?