On New Girl Season 5 Episode 7, Winston was determined to get Reagan to be part of their group of friends. He decides to follow her around and eventually catches up with her while she's out running. Reagan tried to tell Winston she wasn't one to become friends with people because of how much she moves around, but before she can say anything else a woman Reagan had a relationship with confronts her. Apparently the woman was still under the impression they were still together and Reagan starts getting nervous around her, but pretends like they are still together.

Winston questions Reagan about it and she admits she has never broken up with anyone. Winston agrees to help her learn how to break up with people and gives her pointers because he has been on the tale end of many breakups. Reagan tries to take his advice, but ends up leaving Winston as the one to break up with the woman for her. Winston brings the woman back to the loft where he forces Reagan to confront her feelings and be honest. Reagan finally breaks up with the woman and thanks Winston, as well as the other roommates, for their help.

Want to hear all of the ways Winston has been broken up with? Go watch New Girl online now via TV Fanatic.