Savannah Chrisley is marking two major life events at once. During the Tuesday, October 27 episode of her "Unlocked" podcast, the 29-year-old revealed that her boyfriend, Jason, proposed during a trip to the Cayman Islands, a destination she described as the couple's "happy place." The disclosure arrived the same day she announced her pregnancy on Instagram.
Chrisley, a former star of "Chrisley Knows Best," told listeners that she and Jason began dating in July, meaning roughly five months passed before the engagement. She dismissed any concern about the pace of the relationship, saying that time is not the measure of how well two people come to know each other. In her view, three months with someone can reveal more than a full year.
The proposal itself unfolded in stages. Chrisley recounted that Jason had been carrying a ring in his backpack during their December visit to the Cayman Islands without her knowledge. She said she did not have to snoop to discover it: while Jason was retrieving a charger from the bag, he left a box on the counter, prompting her to wonder aloud whether it was what she suspected.
The couple later traveled to a second island that Chrisley described as extremely secluded. There, she noticed Jason seemed distracted and asked what was happening. According to her account, Jason was texting one of her friends to say he believed the location was the perfect place to propose. The friend collected the ring and flew by helicopter to the island, later telling the couple that their afternoon flight had been delayed by an hour.
As the pair prepared to leave for the airport, Jason led Chrisley to a setup featuring flowers and champagne. She assumed he was simply being romantic and had no inkling of what was planned, having spent the day in the ocean and in a swimsuit with her hair and makeup undone. The moment took a comedic turn when Jason could not locate the ring, which had been hidden in a tree, before he eventually proposed.
Chrisley recalled that Jason framed the gift without pressure. "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 quoted him as saying on the "Unlocked" podcast. She added that he never insisted she interpret the ring in any particular way.
The former reality star said she was in such shock that she began to cry. She praised the ring as everything she had ever wanted and called the experience the most magical and amazing in the world. The entire proposal was filmed, leaving the couple with videos and photographs of the occasion.
The pregnancy announcement has also reshaped the couple's wedding timeline. Chrisley explained on the podcast that the ceremony had been scheduled for January 9, 2027, and has now been pushed back a few months to May 2027. "And that is because we got the surprise of a lifetime," she said on the "Unlocked" podcast.
Chrisley, who had previously been pursuing fertility treatment, described the pregnancy as a major plot twist. She said both she and Jason were shocked and thrilled, and that they are unbelievably excited for the baby's arrival.
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Ava Hart
Ava Hart is a pop culture junkie and loves to share what's happening in Hollywood and what trends are taking the world by storm.
