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"He is getting to know her family," the insider says of the composer, who is currently playing bass in Moulin Rouge! The Musical on Broadway.
"Katie is having a great time with Bobby," the source adds. "He is very kind and happy. He makes her laugh."
Ilya S. Savenok/Getty Images for The Moth
Holmes, 43, and Wooten, 33, first stirred up talk of a budding romance when they were spotted kissing and holding hands on April 28 during a stroll through Central Park in New York City. They also took the subway and visited the Guggenheim Museum.
The Dawson's Creek star's mom Kathy joined them for the afternoon out. She was seen giving Wooten a hug in one picture.
A month after their date, the pair made their red carpet debut on May 26 at the Moth's 25th Anniversary Gala at Spring Studios in New York City, where Wooten presented his collaborator (and former Talking Heads frontman) David Byrne with an award.
RELATED: Katie Holmes Seen Kissing, Holding Hands with Musician Bobby Wooten III — Plus He Hugs Her Mom!
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Earlier this month, Holmes brought Wooden as her date to the the Tribeca Film Festival, where Alone Together — the film she wrote, directed, and stars in — premiered. The two looked sweet on the red carpet, holding hands, laughing, and embracing while posing for photographers.
Wooten recently played at Coachella with Carly Rae Jepsen. He has also been nominated for a Grammy Award in the past, serves as an adjunct instructor at NYU Tisch School of the Arts and is from Chicago — a Midwest transplant like Holmes, who grew up in Toledo, Ohio.
A source told PEOPLE of Wooten in April, "He's an amazing guy, very kind, super talented and just an all-around cool guy."
"He's a highly accomplished bassist and musician, and is as chill and brilliant and funny as they come," the insider added.
Holmes was previously married to Cruise for six years before their 2012 split. She was later linked to Jamie Foxx for several years before they broke up in 2019, and most recently dated chef Emilio Vitolo Jr. for eight months before the relationship ended in April 2021.