Signs Chase Chrisley And Emmy Medders Weren't Going To Last

When it comes to Chase Chrisley of "Chrisley Knows Best," you never know what you're going to get. However, the reality star's relationship with influencer Emmy Medders seemed to be a consistent positive in his life over the past few years. The couple began dating in 2020, and even though they briefly split in 2021, they were back and stronger than ever.

The couple initially announced their engagement in October 2022 via Instagram. "I am the luckiest man in the world, being able to call you mine forever is a blessing straight from God," Chrisley's caption read, per People. "You are the sunshine when it's dark, you are the rain when it's dry. I love you more than life itself and can't wait to live forever with you! To you, my love! Thank you for taking me FOREVER!!"

But after nine months, the two have officially broken off their engagement and called it quits. Chrisley's heartfelt announcement post has since been deleted, along with all other signs of Medders, from his Instagram page. Just a day after announcing the split, he appeared to be in good spirits, posting a selfie on Instagram stories. "God is Good," the reality star's post read.

Chase and Emmy previously split in 2021

In 2021, Chase Chrisley and Emmy Medders parted ways due to mutual lifestyle differences, per Life & Style. "I think that it just came down to we kind of looked at like what we wanted in life, and right now, it's not matching up," Chrisley said.

This could potentially mean that one person was looking for a long-term future while the other wasn't. His mother, Julie Chrisley, had previously maintained that the two were taking things slowly, as engagement rumors were already swirling months before the first split.

After the two reconciled in early 2022, they got engaged just five short months later in October. Chrisley proposed to Medders at the Nashville First Horizon Baseball Stadium, pulling out all the stops. He arranged over 175,000 roses on the field and brought together both of their families to witness the event.

Chase's parents previously cautioned him about marriage

Marriage is no easy feat — which the Chrisleys know well. Todd and Julie Chrisley have been married for almost thirty years, tying the knot back in 1996. Several decades later, the couple hopes to instill the realities of marriage into their adult children.

When asked why she preferred her son to hold off on marriage, Julie told Life & Style that she strongly suggested against it. She said that they definitely needed a bit more development in the relationship department. "You know, they say ... that boys' brains don't develop until they're 28," Julie said. "Mine are probably a little slow, so I'm going to go with 30."

Confirming his mother's concerns, Chase also admitted that when he first met Medders, he had to hold off on the relationship to mature a bit more. "I met her a couple of years ago, but I think that I just had some growing up to do," he explained at the time. "As far as she and I go, we're taking things slow."

Chase's father said that he has bad luck dating

While Chase Chrisley has often found himself at odds with Todd Chrisley's strict rules, choosing Emmy Medders as a wife met his father's expectations. Todd had previously approved of their relationship and was grateful that Emmy was in his son's life.

"Chase has had s*** for luck when it comes to picking people to date," the business mogul stated. "No one that Chase has ever dated has ever been allowed to come to our home, to sit at his mother's table, or to be around us because I felt like he was worth more than what he was settling for. We were not going to be subjected to his bad choices."

When Medders entered the scene, the Chrisleys were happy with their son's decision and accepted her as a member of the family. "God answered that prayer with Emmy," Todd continued. "She is a good, decent, honorable, honest, all-American sweetheart, and her family is just literally salt of the Earth. You do not get any better than her family."

Emmy was taking photos without her engagement ring

Several Reddit sleuths called attention to the change in Emmy Medders' online content. Fans of the influencer first noted the tweaks to her social media in July. They called attention to her unpinning engagement photos from her Instagram page and gradually removing more photos of her and Chase Chrisley together. In response to the question about whether they were still together, one Reddit user commented: "I don't think they are. She keeps taking pics without her ring, and they haven't been photographed in a long time."

Eventually, both Chrisley and Medders unfollowed each other — and "Chrisley Knows Best" fans immediately felt sympathy for both of them. In 2022, Todd and Julie Chrisley were infamously indicted for tax fraud and are currently serving their sentences in prison, and it appears Medders has her own family issues going on. One fan wrote on Reddit: "I feel bad for everything [Emmy] is going through, and the health of her dad must impact every aspect of her life and relationships. Chase, on the other hand, is dealing with his own set of losses and a tricky family dynamic. I do wish them both well on their journey, whether that is independently or together."

Chase wanted to have kids with Emmy as soon as possible

After nearly three years of dating, Chase appeared completely ready to settle down with Emmy. In fact, he was ready to take the ultimate step of commitment: having children — and soon at that. He revealed his hopes for a family on the "Chasin Birdies" podcast in May 2023. "I want to have as many children as she wants to have. I want a big family. I mean, I come from a big family, so I don't ever want an empty house. Family is everything."

Chase admitted that he wanted to have children right away. However, the "Elegant Tans by Emmy" owner was set on getting married before making such a life-changing choice. "I'd have a baby right now, but she wants to get married, do [it] the traditional way, which I respect," he continued. "And it's up to her. It's her body." Perhaps this difference of opinion contributed to their breakup. For now, the ex-couple remains tight-lipped.