Stephen Colletti
Beginning in 2004, Conrad was in an on-and-off relationship with her classmate and Laguna Beach costar. Complicating matters? Kristin Cavallari, Colletti's other main squeeze.
Jason Wahler
Conrad began dating the notorious bad boy in 2005 but called it quits the following year. "Breaking up with Jason was the hardest thing I've ever done," the former MTV reality star later told CosmoGirl! magazine. "I still wanted to be with him but I knew that I couldn't be."
Brody Jenner
After breaking up with Wahler, Conrad wanted a nice guy—and Spencer Pratt's partner in crime fit the bill. "We're attracted to each other, but we don't work," Conrad has said of Jenner, who remains her close friend.
Doug Reinhardt
In the spring of 2008, Conrad went on a few dates with her high school ex. "He moved back [to L.A.] and then it was like, ‘Oh, we'll pick up where we left off'…for a couple of weeks,'" she has said of her short-lived romance with the baseball player. Reinhardt later wooed Stephanie Pratt, sister of Conrad's enemy, Spencer.
Kyle Howard
The California native began dating My Boys star Howard in 2008, though he never appeared on his girlfriend's hit reality show. "By the time I had met Kyle, I had already perfected my 'double life,'" Conrad later told Seventeen. "There was my TV life and my real life." The pair called it quits in 2011.
William Tell
Conrad and the former Something Corporate guitarist were set up by mutual pals on Valentine's Day in 2012. Sparks flew, and in October 2013, Tell—a law student at the University of Southern California—popped the question. "I am beyond thrilled!" Conrad blogged.