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The first season winner was 24-year-old Jes Rickleff from Naperville, Illinois.At the reunion, she revealed that she did not have romantic feelings for Michaels, and that she thought that he should have chosen the runner-up, Heather.
Tamara and Angelique appeared on I Love Money 2, where Tamara was the first to be eliminated, and Angelique came in sixth place.Each week, the women face challenges, the winner of which gets to go on a date with Michaels.Some of the challenges were based on situations that they might encounter if chosen to be Michaels' girlfriend.The show closely resembles its sister show Flavor of Love.
The first season featured 25 women competing to be Michaels' girlfriend.
In April 2008 a breach-of-contract lawsuit was filed against both Michaels and the show's producers by the owner of the mansion, Ray Sahranavard.