Chris Kattan has had a string of high-profile romances. In 1999 he began dating Jennifer Gimenez, an American model and actress. The relationship turned out to be a bit of a fling as the couple reportedly didn't date long, per Famous Fix. They were seen together at the GQ Men of the Year Awards in New York City during their short-lived romance. Kattan also reportedly dated comedic actress Jennifer Coolidge in 2001. Coolidge is known for her roles in movies such as "Legally Blonde," "Click," and "American Pie," and TV shows like "2 Broke Girls" and "Friends." She also had a part in Kattan's famous film "A Night At The Roxbury" (via IMDb).

In addition, Kattan was also romantically linked to his fellow "Saturday Night Live" alum Maya Rudolph. Rudolph, who is the daughter of singer Minnie Riperton and songwriter Richard Rudolph (via Showbiz Cheat Sheet), made a name for herself on "SNL," before going on to star in films such as "Grown Ups," "50 First Dates," and "Friends With Kids" (via Rotten Tomatoes). The couple was reported to have a brief fling in October 2001 before Kattan met model Sunshine Deia Tutt in 2005.