While his friendship with Elton John is remarkable, Grealish has long harboured a dream of meeting Rihanna. Four years ago, in an interview, he candidly admitted his admiration for the Barbadian superstar, saying, "She's pretty, and I like her music." When the interviewer teased him about Rihanna’s fiery personality, Grealish shyly responded, "I think that’s cool."
That dream became reality during Manchester City’s 2024 pre-season tour. After a match against AC Milan, Grealish had the chance to meet Rihanna. Sharing a photo of the moment, he appeared visibly thrilled, dressed in a blue football jersey with a jumper tied around his waist. He placed his arm around the global superstar, capturing a memory he would never forget.
Reflecting on the encounter, Grealish admitted he was left speechless. "In the summer, I met Rihanna during the pre-season tour. After playing AC Milan, I went to see her, and honestly, I didn’t know what to say."