Paula is a transgender woman whom Alan dated in Season 11. She told Alan that she presented as a man named Paul for 40 years.
Jenny takes Alan to a gay club where he meets Paula. The two hit it off, before spending the night together. After the encounter, Paula nervously tells him that she was a man named Paul. Although he was shocked, Alan continued to support her and still dates her looking past her history.
Paula introduces Alan to her ex-wife Rachel who she left after coming out and her transition. After Paula tells Alan he can date anyone in the world, Alan takes Rachel to a club where Paula finds them. It became clear that Rachel still had feelings for Paula, pursuing Alan to get a jealous rise out of her. Paula then realized she still loved Rachel, before she and Rachel kiss and get back together. Alan was not bitter about the break-up, as he took a picture of them kissing and to take for his own pleasure.
- Paula is the first transgender character to appear in more than 1 episode.
- Paula is the second transgender character to date one of the Harpers, the first being Bill who dated Charlie as a woman and Evelyn as a man.
- When Paula came out, Rachel was upset and nearly castrated her to do the surgery for her.
- She is in her early forties, being a couple of years younger than Alan.