Second Date Update With Financial Baggage

26/09/2025 49 min
Second Date Update With Financial Baggage

Listen "Second Date Update With Financial Baggage"

Episode Synopsis


☕ PART 1: The Setup Host Summary:Introduce Kyle, the original dater.Recap Kyle’s version of the date:Coffee date.Casual, fun, extended beyond expected time.Kyle paid, thought it went really well.Tried following up for a second, more formal date — no response from Haley.Transition Line:"So we gave Haley a call to find out what’s really going on." 📞 PART 2: The Call with Haley Live Call/Recap:Haley answers, agrees to talk.Hosts gently introduce Kyle’s name and ask for her side.Haley’s Reveal:She thought Kyle was nice but felt they weren’t aligned.The red flag: Kyle opened up about:Two failed businesses.Declaring bankruptcy.She felt his financial instability doesn’t align with her values or what she wants in a partner.Quote Highlight:“At some point you have to adult.” 📱 PART 3: Kyle Joins the Call Live Reveal:Hosts inform Haley that Kyle is on the line.Kyle responds, feeling blindsided and misjudged.Key Exchange:Kyle explains:He confided in her honestly.Entrepreneurship is a risk, but not a failure.He’s currently working on a new business in solar energy.Tension Peak:Haley pushes back:She’s not interested in being part of a “rebuild.”Feels Kyle isn’t “grown up.”Doesn’t want to “bail someone out.”Kyle's Defense:“Just because it hasn’t happened yet doesn’t mean women should count me out.”Stresses that he never asked Haley for money.Final Words:Haley confirms she’s not interested in a second date.Kyle leaves with dignity — and a solar energy plug. 🎙️ WRAP-UP & HOST COMMENTARY Host Reactions:Discuss the realism of financial baggage in dating.Acknowledge Haley’s right to want stability.Empathize with Kyle’s position as an entrepreneur.Reflect on how many successful people faced failure before success.Key Takeaway:“You can meet someone who’s still building their life — and that might be the best investment you ever make. Or... it might not be your journey. And that’s okay.”See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.