Jared kicks off the real first Monday of 2026 with Mailbag Monday energy, reminding listeners that resolutions start now and inviting everyone to put their brain on the shelf. The first email comes from a self-proclaimed “classy” guy spiraling over a friend’s engagement ring he finds tacky, and Jared’s advice is simple: if no one asked for feedback, keep it to yourself. Next, a listener admits she’s stuck in a two-year-long-distance situation with a man who has never wanted commitment, while dating a “nice and consistent” guy she feels less excited about, and Jared delivers tough love that she’s chasing vacation-mode potential, not a real relationship. Finally, a listener feels awkward chasing friends for Venmo pizza money.
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