Second Date Update: Vacation On Me
Oct 16, 2026 · 18m
Summary
Listener Kyle shares his story of paying for a woman's flight and leaving 34 romantic notes in her hotel room, only for her to vanish without a word. The hosts call Sandra, who reveals she froze due to grief over her late fiancé and fear that the gesture was too good to be true. After hearing her perspective, Kyle and Sandra agree to try again, and the show offers to pay for their next date.
Topics discussed
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Show intro and listener comments
Kyle explains meeting Sandra online
The romantic gesture: 34 notes in the hotel
Sandra cancels and leaves without a word
Hosts recap the situation and call Sandra
Sandra explains she froze due to past loss
Kyle and Sandra reconnect and plan a date
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Hosts reflect on the sweet outcome
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