In Are You The One, there is not one winner or even a single couple who wins. The purpose of the show is for all twenty singles to find their "perfect match" which was determined previously to the show. If the group can all find their perfect match, the group as a whole wins $1 million. So, either the whole cast loses or they all win. They must learn to work together to help everyone find their true love.
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If you're talking about the season that just ended, (which is Season 5 by the way) it was Andy. If you're talking about the actual season one from 2001, then it was Maven and Nidia.
Over 22 seasons, only one person has won the game twice. Sandra Diaz-Twine won in season 8 (Pearl Islands) and season 20 (Heroes vs. Villains).
Kelly clarkson
Season 1 the burger guys season 2 lime truck
risky won