Win a Date with Jill is the fourth episode of season 7. Here, 24 bachelors run for a chance of not only winning $50,000, but also a date with sideline host Jill Wagner.
This is the third gender-exclusive Wipeout competition after Ladies’ Night and Beauty Queens. However, it is the first competition to be male-exclusive.
- Qualifier
- Pillars of Atlantis
- Sucker Punch
- Big Balls
- Play Pound
- Jill's Apartment
- Classic Sweeper
- Fun Slides Platform Spinning Purple People Beater
- First Slide
- Sweeper Gauntlet
- Smack Wheel Slide
- Wipeout Zone
- Catastrophic Cannon
- Shredder
- Hell's Carousel
- Gears of Fear
| Courses | Qualifier | Classic Sweeper | Fun Slides Platform Spinning Purple People Beater | Wipeout Zone | |
| 1 | "Retired Baby Model" Nick Santo | 1st (2:38.9) | 4th | 1st | Winner (01:23.96) |
|---|---|---|---|---|---|
| 2 | "Checkmater" Scott Willson IV | 4th (3:31.3) | 1st ($500) | 4th | 2nd Place (03:01.79)
(left with $500) |
| 3 | "Backyard Cowboy" Josh Clark | 2nd (2:51.4) | 2nd | 3rd | Out of Time (left with $500) |
| 4 | "Stripping Salesman" Zack Wilcox | 7th (3:58.3) | 3rd | 2nd | Out of Time |
| 5 | "Dancing Dentist" Jeremy Sewell | 6th (3:54.3) | 5th | Eliminated | |
| 6 | "Nature's Janitor" Joe Woods | 9th (4:10.4) | 6th | Eliminated (left with $500) | |
| 7 | Brendon Kaplan | 3rd (2:56.3) | Eliminated | ||
| 8 | "Brony" Rodrigo Garcia | 10th (4:23.1) | Eliminated | ||
| 9 | "Mr. Sunset" Nick Sharp | 5th (3:44.1) | Eliminated | ||
| 10 | "Bizarro Fabio" Silas Stojanovic | 11th (4:30.6) | Eliminated | ||
| 11 | "First Kisser" Theodore Chang | 12th (4:36.3) | Eliminated | ||
| 12 | "Canadian" Marc Leclerc | 8th (4:08.6) | Eliminated | ||
Trivia[]
- Both Josh Clark and Joe Woods won $500 for tagging Smallsy in the Qualifier.