Plot

Successful theater agent Charlie Reader lives a playboy's life in New York City. When his childhood friend shows up with a desire to leave his wife, the two are awestruck by each other's lifestyle.

Charlie Reader is a successful theater agent. He is also successful with young ladies. One day he is visited by his old friend Joe, married with three children. Joe falls in love with Charlie's girl Sylvia while Charlie spends his time with young actress Julie.—Mattias Thuresson

Broadway agent Charlie is a man about town with a girl for every occasion. Maybe classical violinist Sylvia tops the list, but she's still just a dame. Best buddy Joe, staying over to take a break from his marriage, watches bemusedly while becoming increasingly attracted to Sylvia himself. When young Julie turns up for audition and rebuffs Charlie's advances it looks like he might be becoming a one gal guy. But she has her own grand plan for her future and if he is to be part of it he will have to make commitments quite awful to contemplate.—J-26

Charlie Y. Reader (Frank Sinatra) is a 35-year-old theatrical agent in New York City, living a seemingly idyllic life as a swinging bachelor. Numerous attractive women --- among them Poppy (Lola Albright), Helen (Carolyn Jones), and Jessica (Jarma Lewis) --- come and go, cleaning, cooking for, and enjoying his charms.

Charlie's best friend since kindergarten, Joe McCall (David Wayne), comes from Indianapolis to stay with him, claiming that the excitement is gone from his 11-year marriage and he wants a divorce. Joe envies and is amazed by Charlie's parade of girlfriends, while Charlie professes admiration for Joe's married life and family.

At an audition, Charlie meets singer-actress Julie Gillis (Debbie Reynolds). She has her life planned to a tight schedule, determined to marry and retire from performing to a life of child-rearing by 22. Although at first she wards off Charlie's advances, she comes to see him as the ideal man for her plans. Julie demands that Charlie stop seeing other women. Charlie balks, but he begins to fall in love with her.

Joe starts keeping company with Sylvia Crewes (Celeste Holm), a sophisticated classical musician and a typically neglected lover of Charlie's. Sylvia is approaching 33 and desires marriage as much as the younger Julie does, but just does not show it the same way.

One day, annoyed by Julie and possibly jealous of Joe's attentions, Charlie blurts out a proposal of marriage to Sylvia. She is thrilled, only to discover the morning after their riotous engagement party that he has proposed to Julie as well.

Joe confesses his love to Sylvia and asks her to marry him. She turns him down, knowing that he loves his wife Ethel and children. Sylvia reminds Joe that girls turn into wives when they marry and she wants the same things Ethel does. On her way out, Sylvia runs into a charming stranger (Tom Helmore) of both wealth and culture who is instantly taken with her.

Joe packs up and returns to his wife. Charlie, his other girlfriends also having moved on with their lives, leaves for Europe for a year.

Charlie returns just in time to see Sylvia marrying the new man in her life. She flips him the bridal bouquet. Julie is also at the wedding. Charlie tosses the flowers to her, then asks her to marry him. She agrees and they kiss.