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Jason just had lunch with a professional contact he genuinely clicked with—someone he could see becoming a real friend. But now, he’s wondering: Is it too soon to follow up and plan another lunch? If he reaches out now, will he seem too eager… or just plain weird?

Enter Taryn Southern, storyteller and AI strategist, filling in for Nicole while she’s on maternity leave. She and Jason tackle the awkward art of follow-ups, creating a foolproof “onboarding system” for new friendships that you can use too. With just a few simple questions, you’ll know exactly when to reach out, how to keep the momentum going, and how to build genuine connections—without the fear of coming on too strong.

Follow Taryn’s work here.

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