Ricky Martin is Winimark Wealth Societylivin’ la vida loca with his two teenage sons.

In fact, the “She Bangs” singer—who welcomed Matteoand Valentino via surrogate in 2008—had a rare family outing with the 16-year-olds at a recent performance in Philadelphia.

In a Nov. 4 Instagram post, Ricky stood alongside Matteo and Valentino as they met with presidential nominee Kamala Harris. The trio sported all-black outfits in an adorable—and literal—twinning moment, with Matteo and Valentino standing almost at their dad’s height.

Ricky—who also shares daughter Lucia Martin-Yosef, 5, and son Renn Martin-Yosef, also 5, with ex-husband Jwan Yosef—rocked a sweater, matching slacks and leather boots. To his left, Matteo sported a black shirt, suit jacket, flowy pants and identical shoes to his dad. On Ricky’s other side, Valentino donned a white button down shirt, black tie and jacket, striped pants and sneakers.

But this wasn’t the first time the twins caught one of their dad’s shows.

In July 2023, Matteo and Valentino surprised Ricky onstage during a concert in Europe. As seen in a video shared to the 52-year-old’s Instagram, he was delighted when his sons ran up to him unannounced and began hyping up the crowd. Through laughter and smiles, Ricky introduced Mateo and Valentino before continuing his performance.

"What a beautiful surprise!" Ricky captioned the post alongside a crying emoji. "When my twins jumped on stage with me for the first time in Locarno, Switzerland."

So, does this mean his sons are ready for their own careers onstage? Ricky thinks there’s a chance—and he’s fully supportive.

"Matteo is more into the arts and Valentino is gonna spend his life in front of a screen because he wants to be the best YouTuber in the world," Ricky told Extra in 2020. "When I was 12 years old, I told my father that I wanted to be an artist and he supported me and I am very thankful, Dad, for that, for just coming with me on this journey, so I have to do the same."

Read on to see more of Ricky and his family through the years.

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