The Tender Trap (1955)

Successful theater agent Charlie Reader (Frank Sinatra) lives a playboy's life in New York City. When his childhood friend, Joe McCall (David Wayne), shows up with a desire to leave his wife, the two are awestruck by each other's lifestyle. While Charlie is busy with his newest girlfriend, marriage-obsessed actress Julie Gillis (Debbie Reynolds), Joe falls in with Sylvia (Celeste Holm), a rebuffed former flame of Charlie's, and the two friends must make different but equally important decisions.