J&J are ready to solve dating again, but first, Jared has a bone to pick with Jorge. Next, a listener is doing just fine in her relationship but wonders what experiences are needed to get her to an engagement. Jordana shares how she and her husband made it past that point, and what hesitations she sensed from the email. The Awkward Encounter is more unhinged than hazardous. Then, another listener is unsure if she should compromise plans with her besties for an important night to her boyfriend. The episode ends with a “Red Flag or Deal Breaker” about bringing up an ex at awkward moments, a SO’s closeness with their ex, and lacking a taste for adventure.

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