Usher's on-stage serenades have become a signature part of his concerts, drawing both admiration and, in some cases, concern from significant others in the audience. The Grammy-winning singer recently recounted an interaction with a professional athlete who wasn't too keen on Usher's flirtatious act.

During an appearance on The Late Show with Stephen Colbert on September 11, 2025, Usher revealed that Mookie Betts, the star outfielder for the Los Angeles Dodgers, had approached him with a playful warning. Betts, who is married to Brianna Hammonds, apparently wasn't thrilled with the idea of Usher serenading his wife during the show.

Usher explained that Betts told him, "No serenade. Leave the cherries at home. No cherries," referencing the cherry-feeding portion of Usher's act. Colbert humorously responded, "That's a man that uses a bat professionally. I would listen".

The "cherry moment" has become an iconic part of Usher's performances. Usher has explained that the cherry bit was created to give women "the freedom to have fun at a concert," describing the gesture as playful and lighthearted. The tradition began during his Las Vegas residency in 2022 and has been a fan favorite ever since. In May 2025, at the Met Gala in New York City, Usher playfully fed a cherry to Sabrina Carpenter, a fellow artist in the audience.

Despite the generally positive reception, some significant others have been less than thrilled with the up-close-and-personal nature of the serenades. Another instance of Usher's on-stage interactions involved Charlamagne tha God's wife. During a Las Vegas performance, Usher gave Charlamagne's wife roses, prompting Charlamagne to joke about it on "The Breakfast Club". He humorously called Usher a "terrorist" for also serenading Doja Cat and Jessica Alba, who were also in attendance.

These interactions highlight the delicate balance between entertainment and personal boundaries. While many fans enjoy the playful and engaging nature of Usher's serenades, some partners understandably feel protective. Usher's ability to navigate these situations with humor and respect is a testament to his experience as a performer. It remains to be seen whether Usher will modify his act in response to these concerns, but for now, the "cherry moment" continues to be a memorable part of his shows.