"Is Brooke Shields a good kisser?" - Andy Roddick reveals how he almost got in trouble with Andre Agassi in hilarious confession

Andy Roddick humorously disclosed how he almost embarrassed himself with an inappropriate question regarding Brooke Shields when he had the opportunity to talk with Andre Agassi early in his career. On the latest episode of his podcast, Served with Andy Roddick, he was expressing his gratitude on account of his foundation's 25th anniversary.

Roddick took this opportunity to shed light on what inspired him to begin the Andy Roddick Foundation in the first place. When he was 17 years old, he found himself sitting next to Agassi during a plane ride. The veteran was in a jovial mood and wanted to share some life and career tips with his younger compatriot.

Roddick was initially tongue-tied, and almost asked Agassi whether his wife at the time, Brooke Shields, was a good kisser. Fortunately, he kept that thought to himself and avoided a massive faux pas.

"I'll tell you how it started. I was on an airplane with Andre Agassi. I was 17 years old and I got to ask him some questions. He said, 'Okay kid, 25 minutes left in this flight. What do you got?' And so I was like, 'Oh man, what was it like, you know, is Brooke Shields a good kisser?' No, I didn't ask that," Roddick said.

Roddick instead asked Agassi if he had any regrets, to which the latter responded by saying he wished he had started his own charitable efforts even earlier. This struck a chord with Roddick, who was well aware of Agassi's involvement in humanitarian causes. This ultimately inspired him to start something of his own.

"Is there, you know, not knowing fully his history from his book, I said, 'What is your biggest regret?' And he said, 'Not starting my foundation early enough.' And that is something that stuck with me in my soul because Andre is one of the most generous philanthropists that Earth has ever seen and what he's done for entire areas of Las Vegas is unprecedented. And so for him to have done all that and still think, hey you know what, I wish I could have done more. We started off the foundation then," Roddick said.

Roddick's chat with Agassi took place in 1999, and launched his foundation in 2000. He was just 18 years old at the time, and the top-ranked junior in the country.

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Andy Roddick aims to empower underprivileged youth with his foundation

Andy Roddick with his wife Brooklyn Decker. (Photo: Getty)

Andy Roddick had only one goal in mind when he launched his foundation, to empower youth who wouldn't otherwise have the opportunities to succeed. He has been successful on that front, with his foundation completing 25 years.

Roddick's foundation has raised over $30 million since its inception. His foundation recently held another charity gala on November 10, 2025, which was headlined by Grammy-award winning artist Wyclef Jean.

Roddick is optimistic of raising more funds after the conclusion of this week's gala. They raised around $1.3 million after the 2024 edition of the gala, and will hope to better that amount this time.

Edited by Rohit