Frank Sinatra Shared the Long List of Qualities He Looked for in a Woman

Frank Sinatra was married four times and had a number of other significant romantic relationships in his life. While he dated many women with various backgrounds and personalities, Sinatra had a specific set of qualities that he wanted to see in his dates. He shared the kind of woman that he would most want to be with.

Frank Sinatra was married to four women

In 1939, Sinatra married his first wife, Nancy Barbato. The two met as teenagers on vacation on the Jersey Shore. Their relationship and marriage began before Sinatra was a famous singer. Barbato was with him as he climbed his way to success. Once he achieved it, she dealt with his frequent infidelity.

One of Sinatra’s extramarital affairs was with Ava Gardner, who he married less than a week after finalizing his divorce with Barbato in 1951. While many believe she was the love of his life, their relationship was volatile and characterized by bitter fights. They divorced in 1957.

In 1966, Sinatra married Mia Farrow, who was 30 years his junior. While they remained close for decades, they divorced after just two years. Sinatra wanted Farrow’s career to revolve around him, but she craved autonomy over her work.

In 1976, Sinatra married for the fourth and final time. His relationship with his wife, Barbara Sinatra, began as an affair but ended up being his longest marriage. They remained together until his death in 1998. 

He had a laundry list of qualities that he wanted in his potential romantic partner

In a 1965 interview with the Hartford Courant, reporter Hedda Hopper asked Sinatra what he looked for in a woman. 

“I like an intelligent woman,” he said. “When you go out on a date, it shouldn’t be a staring contest. I don’t like a girl who says, ‘Hello, may I sit down?’ and that’s it.”

The other qualities Sinatra sought out pertained to a potential date’s habits.

“I don’t like chain smokers — it’s a serious disease in women today,” he said. “The first thing I notice about a woman is her hands — how they’re kept — good grooming is important.”

He also had hyperspecific preferences for how a woman smelled.

“I don’t like walking perfume ads, although there are some perfumes I do like,” he said. “There’s one … Tuvache, that’s it, a faint gardenia scent. I like that.”

Finally, Sinatra had an opinion on how his date dressed.

“I don’t like women who dress in extremes,” he said. “I like nicely tailored elegance — conservative. And I don’t like topless bathing suits.”

He admitted that he had never seen someone in a topless bathing suit, but he thought he’d dislike it if he did.

Frank Sinatra had relationships with a variety of different women

While Sinatra did marry four times, not all of his important relationships reached that stage. He was good friends with Judy Garland, but the pair also had an on-and-off affair, trading love letters back and forth. He had a days-long engagement to Lauren Bacall and nearly proposed to his Ocean’s 11 co-star Angie Dickinson. 

“I actually didn’t want to marry him,” Dickinson told CBS News. “So, I didn’t want him to ask me to marry him. ‘Cause I didn’t wanna say no to Frank Sinatra!”