Shelby was Winston's booty call prior to his career in Latvia for basketball. He called her up after his return, thinking he can pick up with her where he left off. Shelby makes it clear she has no intention of going home with him, considering he took her out at her place of work and talked about himself for an hour. He later realizes his mistakes and returns to apologize (Jess & Julia).
Shelby decides to give him a chance, on Valentine's Day. Given the nature of this holiday, Winston thinks it's an official date, so he is surprised when he finds she invited all of her friends over for wine and pedicures. He decides to join the girls for some brownie points. After her friends leave, she re-invites Winston back in to her apartment for the real date.
Shelby goes out with Winston and Schmidt to a bar for trivia night. Schmidt is amazing at the game, and she is very impressed. This leaves Winston in very jealous state and ends up memorizing all of the trivia cards just to impress her. She figures it out the following night, when Winston barks out incorrect answers, sometimes before the question was even asked. Shelby was flattered, and she rewards him by making their relationship official by the end of the night.
- Dated Winston in Seasons 1 and 2
- Made her own costume on Halloween, stapled stuffed animals to a cape (Reigning cats and dogs).
- Didn't have sex with Winston for a long time, and was the ultimate cause of their break up.