Rob Thomas Reflects on Missed Opportunity with Alyssa Milano at a Concert: A Moment We’ll Always Wonder About

Rob Thomas in New York City in December 2025; Alyssa Milano in October 2025 in New York City.
Credit: SiriusXM and Pandora; John Nacion/Variety via Getty

NEED TO KNOW

• Rob Thomas reflected on a missed connection with Alyssa Milano
• During a performance at SiriusXM and Pandora Present PopRocks The Holidays, he revealed he once “blew” his chance with the actress
• Thomas, Lisa Loeb, and the Goo Goo Dolls all performed at the event on December 9

Rob Thomas, frontman of Matchbox Twenty, reminisced about a missed opportunity with actress Alyssa Milano during a recent performance. The event, SiriusXM and Pandora Present PopRocks The Holidays, took place at Hammerstein Ballroom in New York City on December 9.

At 53 years old, Thomas addressed the crowd and shared that Matchbox Twenty would soon celebrate its 30th anniversary. He humorously noted a decade of his tenure that he does not fully recall, which led to his mention of Milano.

Reflecting on their near-connection years prior, Thomas pointed to a balcony in the same venue where he tried to woo Milano. “I blew my chance with Alyssa Milano,” he told the audience. “We’ll never know, will we?”

Rob Thomas in New York City in December 2025.
Credit: SiriusXM and Pandora

In a previous interview with the Associated Press in 2019, Thomas disclosed that Milano was his childhood crush. While PEOPLE has reached out to Milano for a comment, her response remains pending.

Following his affirmation about Milano, Thomas inspired the audience with a heartfelt message about joy before performing his song “Little Wonders.” He stated, “Happiness will meet you if you meet it halfway. If you show up to the party, happiness will have a drink in its hand,” emphasizing that the moments of joy are within reach each day.

Thomas has been married to Marisol Maldonado since 1999, and he once expressed in a 2000 interview, “I knew the second I kissed her that I would never, ever kiss another person.” Over the years, he has spoken about their relationship, describing their commitment to each other as enduring and unwavering.

The event featured performances by Lisa Loeb and the Goo Goo Dolls, showcasing a blend of talent and shared experiences in the music industry.