Should You DM the Girlfriend If You’re the Other Woman?

In this episode of U Up?, Jordana Abraham and Jared Freed dive into two listener emails that spark rich discussions on modern dating dynamics and personal accountability. The first email centers on a woman who discovered she was the 'other woman' in a college relationship and chose to message the girlfriend via Instagram, only to later unsent the message out of anxiety. The hosts debate whether this act was petty or prudent, with Jared arguing it was a necessary act of honesty in a close-knit college environment, while Jordana emphasizes that the emotional weight of the situation—eight years later—suggests unresolved guilt and a need for closure. The second email comes from a 32-year-old man frustrated by a string of first dates with women aged 30–32, where he feels he’s being evaluated like a job candidate. The hosts dissect his transactional mindset—tracking exact costs, tips, and rejection patterns—and conclude that his frustration stems from internalized expectations, not the women themselves. They urge him to delete the dating apps, reconnect with friends, and process his past relationship trauma before dating again.