18 TV Friends Who Dated the Same Person

Ray (Alex Karpovsky) dates Shoshanna (Zosia Mamet) during Girls' second season, but things come to a sad end after Shosh breaks up with him because of his negative attitude and lack of ambition.

In season three, Ray strikes up a fling with Marnie (Allison Williams) — who, coincidentally, is the ex-girlfriend of his friend Charlie (Christopher Abbott). Ray carries a torch for Marnie throughout her relationship and short-lived marriage in season five, and also manages to become friends with Shosh again.