After vowing to start dating men who are her equal and who share a similar lifestyle and work ethic, Jen leaves her house for patio drinks in the city and shoots her shot with a younger guy by sending him a shot to his table and finds out that old habits really do die hard. To get herself back on track, she turns to a little self-love and a refresher course on how to ask someone out with YouTube relationship expert Kimberly Moffit.

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