“Completely Inappropriate”: Harry Connick Jr. Gets Candid On How Frank Sinatra Kissed His Victoria’s Secret Model Wife On The Lips

Date November 20, 2019

Frank Sinatra was a great musician and for many, he was the greatest vocalist of his generation. A lesser-known fact about Sinatra was that he loved doing puzzles and he would rather sit down doing them that do anything else.

But another not so secret fact about Ol’ Blue Eyes is that he was a notorious womanizer whose boyish smile charmed women that were attracted to his star power and personal charm.

Harry Connick Jr. recalls how one time, he found himself in a very unpleasant situation when Frank Sinatra kissed his wife on the lips, right in front of him!

Frank Sinatra got inappropriate with Harry Connick Jr.’s woman

They say that first impressions last and Harry Connick Jr will never forget what happened the first time he and his wife met Frank Sinatra.

Speaking to This Morning on Tuesday, Harry revealed that the first time he tried to sing for Sinatra, he totally “blanked out” because of pressure.

When he later approached Frank Sinatra, the only words he had for him were, “That was unpleasant” since he had totally flopped his attempts to sing. But while Harry had disappointed Sinatra, his wife and former Victoria Secret’s model, Jill Goodacre, had caught his fancy.

In a move that Harry would also consider “unpleasant,” the My Way singer told Jill that she was beautiful, hugged her, and in an awkward turn of events (for Harry) kissed her on the mouth!

The experience was an unexpected turn of events and since then Harry never looked at Sinatra differently.

I’ve never been able to sing for him again. it was probably unacceptable then… obviously its completely inappropriate.

Since the weird first encounter, Harry continued to build himself as a jazz musician with 2 Grammys for Best Jazz Vocal Performance under his belt.

Harry and his wife Jill have been married for 25 years

Despite his wife’s infamous kiss with Frank Sinatra, Harry and Jill have been together for 25 years, which is impressive for people in show business.

Speaking to Variety, Harry disclosed that having a close bond with his wife shaped him as an artist and the singer credits his success to love and companionship.

The deeper I connect with my family — and every day we grow deeper and deeper in love with each other — the freer I am to be more creative.

It’s amazing that for Harry Connick Jr. his family is his strength, which is a great lesson to all couples. Together, Harry and Jill have 3 daughters, Georgia, Sarah, and Charlotte.