When does financial honesty cross the line into exploitation? Tim and Gwen tackle three messy money dramas. First, a single dad is forced to ask his new girlfriend to pay for dates and groceries because his ex-wife refuses to contribute to their kids' expenses. Is he the asshole, or is he just a victim of a bad divorce? Next, a financially organized woman is dating a younger partner who keeps all his savings in one checking account, driving her crazy. Is his disorganization a huge red flag, or is she unfairly parenting him? Finally, a 30-year-old who hit FIRE needs to know: what do you tell your dates you do for work when you don't have a job title?

Gwen mentions https://retireoften.com/ from Jillian Johnsrud