Although he'd been roommates with Nick and Schmidt long before Jess moved in, Winston Bishop was playing D-Club ball in Latvia when she arrived. But he when he lost his post as point guard in the Latvian Basketball League he returned to the States.
It became apparent right away that he may be the smartest guy in the pad as he cleverly manipulated Schmidt into giving up the big bedroom. But he also showed that he's a good guy. Even though he really wanted the room, he relinquished his "Top Dog" status and eased up on Schmidt when he could've gone in for the kill.
That's not to say Winston doesn't have a killer instinct. He has to be the best handbell player in his group, and he's determined to dominate in the trivia challenge at the local bar.
But he's also got a lot to learn when it comes to the ways of women. When he pursued Shelby, an ex he didn't treat all that well, she rebuffed his advances. Then his competitive nature kicked in, making him want her all the more.
Upon scoring a date with Shelby, Winston's softer and goofier side shone through in a celebratory dance. He followed that with a show-tune-fueled trip to Mexico to try to win her back after she granted him the space he'd asked for in the relationship.
Winston has started to get his post-Latvian life on track after landing a job as a research assistant for a notoriously difficult sports radio host. And with Shelby by his side, he just may be the only roommate who has things fully under control.