169. “We flew to Lisbon for Taylor Swift, but my $5 beer is the problem?”

Annie’s 39 and Emery is 43. Although they have a high combined income, Annie makes 5x more than Emery. This leads to frustration over small purchases, like an extra drink at dinner—while they’re on vacation in Europe. Emery also manages their two rental properties even though they earn $0. He’s desperate to sell, but Annie is convinced of their long term value. 

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