It's Jake and Tiffani's three month and two day anniversary. Jake agrees to go on the dating game as contestants along with Sly and Tony. To Jake's surprise, he ends up winning the date, and decides to keep it a secret from Tiffani. She finds out, causing her to break up with him again. Meanwhile, Tony gets to meet his idol, gameshow host, Milt Bradley.
| Name | Type | Role | |
|---|---|---|---|
| Marcus Smythe | Guest Star | ||
| Karen Roe | Guest Star | ||
| Rachel Parker | Guest Star | ||
| Dru Ramsom | Guest Star |