Before Tom Cruise, before Chris Klein, there was . . . Arthur Colombino?
The singer -- whose Arthur Colombino Band released new album, This Life, last month -- tells Us Weekly he briefly dated the now-single Dawson's Creek actress, 33, back in 2000.
Then a waiter at an uptown club in NYC, Colombino caught the eye of the rising star one night as she was hanging out with her Dawson's Creek pals -- including show creator Kevin Williamson, who brokered an introduction.
"Kevin came up to me and told me, 'My friend Katie wants to meet you,'" Colombino tells Us. "I knew who she was. I didn't want to bother her."
After a "great conversation," Colombino says, Holmes invited him for drinks -- and the twosome embarked on a four-week romance as the star flew in and out of NYC while shooting Wonder Boys with Michael Douglas and Tobey Maguire in Pittsburgh.
"It was a very short lived thing, but it was nice, she was sweet," the singer recalls. "We'd go out to dinner. I took her downtown. I don't think at that point she had ever been downtown," he said of Holmes, who recently moved into a $12,500-a-month Chelsea apartment with daughter Suri, 6.
How was the future Mrs. Tom Cruise back in the day? "Extremely intelligent, very goal-oriented," Colombino says -- not to mention funny! "She had a really funny, quick-witted sense of humor. Almost like a Woody Allen, quick-line sense of humor, which I didn't expect," he raves. "She was really sweet and very charming."
Another priority for a just-out-of-her-teens Holmes? "Her family was very important to her," he says. "One of the things she said about her mother and father was that they wanted her to be a woman. She was not a girl, she was a woman. She definitely had integrity, which you don't see."
Although both Holmes and Colombino soon relocated to Los Angeles, they never crossed paths again. Holmes met American Pie star Klein, 33, later that year in 2000, and they became engaged in 2003. Holmes and Klein parted ways in early 2005; months later, she and Cruise, 50, debuted their own relationship to the world.
Colombino wishes nothing but the best for Holmes as she starts her new life post-Cruise as a single mom. "She's one of the people in Hollywood that has a cool demeanor, seems like she loves being a mother," says Colombino, who himself is now a divorced, single dad on amicable terms with his ex-wife. "I think there's a lot of people in her corner."
This article originally appeared on Usmagazine.com: Katie Holmes' Former Fling Speaks Out