Original Broadcast Date: February 13, 2022
| Song / Segment |
| Introduction Monodrone - Black Rings (Nightcap Too Much Affection Edit) |
| Opening Theme - Tales of the Wizard of Oz 🍁 |
| Living Voices - Valentines Candy |
| Willie Nelson - Valentine |
| Stompin Tom Connors - Valentine Song (My One and Only Valentine) 🍁 |
| George Jones - Candy Hearts |
| David Bowie - Valentine's Day |
| Bruce Springsteen - Valentine's Day |
| Dore Alpert - Won't You Be My Valentine |
| Serge Gainsbourg & Jane Birken - Je t'aime .. Moi Non Plus |
| Charlotte Gainsbourg - Deadly Valentine |
| P'tit Belliveau - Income Tax 🍁 |
| Nikkie Gallant - Lights 🍁 |
| Nikkie Gallant - River 🍁 |
| D'orjay The Singing Shaman - Haunting 🍁 |
| D'orjay The Singing Shaman - Soul Retreival 🍁 |
| Sam Cooke - Cupid |
| Connie Francis - Stupid Cupid |
| The Diasonics - Gurami |
| Nightcap Storytime Time Machine - My Favorite Husband (Valentine's Day) |
| Yonder Mountain String Band - Dancing in the Moonlight |
| The Weakerthans - Tournament of Hearts 🍁 |
| Monodrone - Late Nights 🍁 |