Jack has 4 dates set up, all on ONE day, hilarity ensues
| Actor | Role |
|---|---|
 Jacky SunJack | Jack |
 Henry RoesslerCupid | Cupid |
 Charlie KryCameraman | Cameraman |
 Dashiell SearsSound | Sound |
 Matthew MinardiHarold the Handyman | Harold the Handyman |
 Henry SaxtonJacob Octorious | Jacob Octorious |
 Nick WeigelGlen | Glen |
 Ben "Junior Ben" PettersonWoody, from hinge | Woody, from hinge |