Brooke and Jeffrey: Second Date Update Brooke and Jeffrey: Second Date Update

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

Ad: Eczema treatment with Ebclis Ad: Multiple sclerosis treatment with Kesimpta 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 Ad: Weight management with Zepbound Hosts reflect on the sweet outcome Ad: Weight management with Zepbound Ad: California manufacturing and agriculture
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