Savannah Chrisley Says 'Timing Is Nothing' as She Reveals Pregnancy and Secret Engagement to Older Fiancé Jason: 'The Most Magical, Amazing Experience'

Savannah Chrisley is celebrating two major milestones after revealing she is pregnant and engaged to her boyfriend, Jason.

The former Chrisley Knows Best star shared details of his romantic proposal in the Cayman Islands on her podcast.

During the Tuesday, October 27, episode of her Unlocked podcast, Chrisley, 29, shared the exciting news.

"Jason and I started dating in July [2025], so... five months," she detailed. "Timing means nothing, guys, OK? But back in December, Jason and I were in the Cayman Islands, and little did I know, he had a ring in his backpack."

The star said she "didn't have to snoop" to find it.

"Jason was getting a charger out of his backpack; I think I called him in the other room," Chrisley remembered. "He came in there, and then he left a box on the counter. I was like, 'Oh, my God, is that what I think it is?' But I didn't know, to be, you know, 100 percent."

Jason took Chrisley to another island, which she described as "extremely secluded."

"It was the coolest thing ever," she expressed. "But... there was a point in time to where I saw that he was, like, distracted. And I'm like, 'What's going on?'"

Jason had secretly messaged one of Chrisley's friends, telling her he thought they were in the perfect spot to propose.

The friend flew to the island with the ring and later told the couple their flight that afternoon had been delayed by an hour.

As the pair prepared to head to the airport, Jason led Chrisley to a setup with flowers and champagne.

Before presenting the ring, Chrisley shared the sweet words Jason told her.

"When he gave me the ring, he was like, 'Before I open this, I just want you to know that this is just an expression of love to you. This can be whatever you want it to be. This can be an engagement ring, a promise ring, a cocktail ring for all I care. I just want you to know how much I love you,'" she recalled.

"And there was no pressure ever put on me to, like, 'You have to accept this as this,'" Chrisley added.

She acknowledged that the proposal came "really quick" into their relationship.

"I feel like you could find out more about a person in three months than you did in a whole year of being with them," the influencer declared.

Chrisley said she was "in such shock" during the proposal that she began to cry, later praising the "insane" ring as "everything I ever wanted."

"It was just the most magical, amazing experience [in] the entire world," she gushed. "It was all filmed, and so we have videos of it, photos of it, and that's just us. And I absolutely love him for who he is and creating those special moments for us."

On October 27, Chrisley also announced her pregnancy with a sweet Instagram video.

The "major plot twist" caused the couple to adjust their wedding plans.

They had originally scheduled their ceremony for January 9, 2027, but have since pushed the date back to May 2027.

"We both were so shocked, so thrilled," the mom-to-be said. "God's hand was written all over this. ...We are unbelievably excited and cannot wait for this baby to get here."