It doesn't go so well, and neither does the karaoke.
"Do you feel like your life could be written into a great country song?" Shelton asks his co-star, who thinks it "totally" could.
But as she starts filling in the country superstar in on the details of her life, it quickly becomes apparent maybe not.
"I'm just a hot mess. Drinking and partying," Handler says before adding, "I would love an interest. No one's interested in me, so let's make one up ... I guess I have to wait for somebody to get divorced or something."
"That's a country song," Shelton says. "Now we're getting there."
But you know what doesn't fit in a country song from Handler's life? "I don't like kids. What about that?"
"So basically, it's about a lonely, miserable, white Jewish girl who's going to have to wait for somebody to get divorced," Shelton says. "You like where it's going?"
Handler approves. Country fans probably wouldn't.
Watch their horrible rendition of a-Ha's 1985 hit "Take on Me" below.