The Chelsea Lately host split from the hotelier in November 2011 after six months of dating but has since decided to give the romance another chance.
Appearing on Marc Maron's WTF Podcast, Handler explained her reasons for ending the relationship, as well as choosing to try again.
"It was extremely time consuming and it was really, really hard for me to focus on anything at all. He lived in New York and I lived in LA, and it was a constant back and forth, flying and meeting each other," she said.
"[It] kind of took the wind out of me. . . it drained me from my career, it drained me from my work. I wasn't focused on anything. It was just stress. It was just exhausting. But I prefer a long distance relationship because I don't really want to deal with someone on a daily basis."
Handler recently said that she would not be friends with Angelina Jolie as she does not believe that the actress is the kind of woman she could trust.