It’s Mailbag Monday from Delray Beach, and Jared’s inbox is doing what it does best: exposing the chaos we all pretend isn’t happening. First up, a “situationship” that’s giving off mysterious relationship anxiety vibes, an age gap, daily drinks, and a whole lot of “we” language for something that isn’t actually a “we.” Then a freshly single 31-year-old wonders if her breakup for political differences was valid. Was her breakup valid? Finally, a NYC listener needs a birthday dinner strategy when her favorite one-on-one friend turns into a group-setting chaos grenade. Jared lays out the only real options: set boundaries, make it their choice, or keep the reservation (and your peace) on lockdown!

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