The actor has remained fairly private about his dating history, but there are at least three famous ladies who came before Allen—Alison Sudol, Julia Stiles and Maria Thayer.
Sudol and Harbour were dating as recently as May 2019, with Sudol posting a sweet photo of her and Harbour wearing matching T-shirts on Mothers Day in support of the non-profit The Mother Lovers. (The two don’t have any children together, in case you were wondering.) You likely recognize Sudol either from her role as Queenie in Fantastic Beasts and Where to Find Them or as the singer A Fine Frenzy. No word on why or when the couple split, but they did spend part of the Christmas holiday with one another and appear to have remained close friends.
Between 2011 and 2015, Harbour was in a pretty serious relationship with none other than ’90s film and feminist icon Julia Stiles. The two lived together in NYC for part of those four years, although their relationship somehow managed to fly under the radar (perhaps because Harbour wasn’t as well known as he is now). Stiles most recently starred in Hustlers alongside Jennifer Lopez and Constance Wu.
Last (or should we say first?) but not least is actress Maria Thayer. She and Harbour dated from 2009 to 2011, just after she appeared in Forgetting Sarah Marshall as Jack McBrayer’s sexually frustrated new wife.