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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 The 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.
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