Dean, Jared and Vanessa discuss the whirlwind relationship of Ariana Grande and Pete Davidson, and Jared tells us if he’s ready to take his relationship to the next level. Then they’re joined by Chelsea Leigh Trescott, a break-up expert, for some help on how to not suck at breaking up. And, after reflecting on their experiences with The Bachelor, they talk about if it’s okay to date a friend’s ex.