Alfie

Alfie is a charming and womanizing limousine driver in Manhattan who lives a carefree life of one-night stands and casual relationships. However, when his friend Marlon gets back with his ex-girlfriend Lonette, Alfie finds himself feeling left out and begins to question his lifestyle. He then embarks on a passionate but tumultuous relationship with Nikki, a beautiful but unstable woman, and struggles to keep up with her mood swings. As he tries to find a way to make their relationship work, he also faces a health scare that makes him realize the importance of finding someone to love and living life to the fullest.

You can stream Alfie on: Netflix Amazon Store

Some movies that have similar genres and were produced around the same time as Alfie include First Daughter, No Reservations, Secretary, Wild Child, Varsity Blues, Jersey Girl.