‘You, Me & My Ex’: Matt Breaks His Proposal News to Ex Chelsea in Exclusive Sneak Peek

With Matt on the precipice of proposing to girlfriend Kenzie, he’s bringing in ex-girlfriend Chelsea to help him plan the special day – even if she thinks he shouldn’t be getting down on one knee at all. In a PopCulture.com exclusive sneak peek of Monday’s all-new episode of You, Me & My Ex, Matt breaks the news that he’s going to pop the question soon when he and Chelsea are out drinking at their favorite bar. 

“So dude, I’m thinking about proposing to Kenzie soon,” he tells Chelsea, who pauses for several seconds before asking, “Why?” Matt answers, “Cause I love her. You know, it’s that time,” earning only more of a shocked stare from his ex. Chelsea’s concerns aren’t with Kenzie, she explains later to the camera, but with Matt. “I don’t think Matt’s ready to get married and settle down,” she says candidly. “He gets bored and doesn’t like being stuck in a rut and likes to do things that are bad just to keep it interesting… like inviting me to come live with him.”

Despite her skepticism, Matt says he does want to “run some ideas” by Chelsea on how he’s going to propose, “because I have no damn idea what I’m doing.” Chelsea counters, “I think that you should not propose and not get married for a very long time. [That] would be my honest opinion.” Matt is undeterred, however, despite the problems he and Kenzie have been having since Chelsea became their new roommate. 

“All I’m saying is that I’m ready for it and I want you to be a part of at least the experience, like ring shopping with me,” Matt insists. “Will you at least do that?” He adds to the camera later that it can “definitely hurt a little bit” when Chelsea is so “negative” about his plans, saying, “I mean, here I am planning the biggest day of my life and she’s griping about it. Like, support me, what the hell?” 

Turning to Chelsea one more time, he tells her, “I need somebody to turn to, and you are my right-hand man,” insisting how much he will appreciate her help. Raising a beer, Chelsea gives in: “Cheers to that, I’m your right-hand man,” she says, as Matt agrees, “You are my right-hand man.” You, Me & My Ex airs Mondays at 9 p.m. ET on TLC.