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Frank Sinatra loved to spend long nights at restaurants, except when his wife took him to fine dining establishments. The singer had a specific list of restaurants he liked to frequent when visiting various cities. Unfortunately, there wasn’t much overlap between the places Sinatra liked and his fourth wife, Barbara Sinatra, enjoyed. When she did manage to get him to her preferred spots, he chose to eat his dinner in the car.

Frank Sinatra has his hand around his wife Barbara Sinatra's shoulders. They both have yellow sweaters hanging over their shoulders.
Frank Sinatra and Barbara Sinatra | Harry Langdon/Getty Images

The ‘My Way’ singer never wanted to dine alone

According to those who knew him well, Sinatra would always prefer to dine with a table full of friends.

“He grew up as an only child, and he vowed that, as an adult, he would always have people around him,” radio host and Sinatra dinner guest Mark Simone told the New York Post.

He’d pack restaurant tables so full of people that many of his guests didn’t even have the chance to speak to him.

“If he invited you to dinner, you’d be honored,” Simone explained. “But dinner was 27 people. You’d be lucky if you were 14 seats away from him.”

Frank Sinatra made an exception to his solo dining rule when his wife took him to nice restaurants

The restaurants Sinatra frequented served the food he liked and catered to his every whim. One of his favorite meals was reportedly breaded, pounded veal with spaghetti and red sauce on the side, and he liked restaurants like Patsy’s in Manhattan that would serve it to him. 

His friends agreed that he did not like fancy restaurants, though he did like specialized attention from the restaurant staff.

“He went to places where the staff would protect him,” Pete Hamill, author of Why Sinatra Matters, said. “There’d be three waiters hovering. They sealed him off from the other customers, usually the guys who were stewed and wanted him to sign their ties or something.”

Sinatra’s fourth wife, Barbara, liked Le Cirque, an upscale French restaurant in Manhattan. When she could convince him to join her, he reportedly took his dinners in the car. Even when he did enter finer establishments, it seems that he preferred the bar to a table. When Sinatra was at the Colony, another New York restaurant, newly appointed maitre d’ — and eventual owner of Le Cirque — Sirio Maccioni suggested Sinatra have his drink at his table instead of the bar.

“Listen, kid, let’s not have a fight on our first day,” Sinatra responded, per GQ.

Frank Sinatra’s wife had a contentious relationship with his children

Sinatra and his wife disagreed on restaurant preferences, but she had a much fiercer disagreement with his children. The week before the couple’s wedding, Sinatra’s daughter Nancy cried for a week. She mourned the fact that the wedding likely meant that her parents would not end up together. She also resented the fact that Sinatra had to get an annulment from his first wife in order to marry Barbara in a Catholic Church. 

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“I found the concept of annulment shocking,” Nancy wrote in the book Frank Sinatra: An American Legend, “and my brother (the late Frank Jr.), sister and I were concerned about how it would affect our mother.”