In this Mailbag Monday, Jared is in Richmond, living his best suburban comic life! A listener with a crush in her tight-knit Spanish class worries about ruining the group vibe, and Jared tells her to skip the overthinking and text with confidence. Another listener hears from the guy who once wouldn’t commit, now cheating on his girlfriend with her, and Jared explains that it’s about comfort, not connection. Finally, a couple debating a $5K destination wedding in Mexico with a toddler gets Jared’s advice to either decline gracefully or treat it like a sitcom-style vacation and just enjoy it.

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