Courting Courtney (1997)

Filmmaker Nick has decided to make a documentary about his best friend Courtney's love life. Courtney, a schoolteacher, has had a two-year on and off relationship with a guy who can't commit; she's also tried video-dating and a women's group. She never thought she'd have a problem finding the right guy and falling in love, but as she gets closer and closer to 30 she gets more and more desperate. Nick, on the other hand, is having as much trouble finding the right girl, and when his true feelings for Courtney come to light, they have to decide whether or not to stay just friends.

Unfortunately the movie Courting Courtney is not yet available on HBO Max.