On the latest episode of 'The Bachelorette' alumna's podcast, the newly engaged pair looked back at how Woolard popped the question
Last month, PEOPLE exclusively confirmed that the former Bachelorette, 28, got engaged to Woolard at Bolt Farm Treehouse on Aug. 24 in Whitwell, Tennessee. And on Wednesday, the couple finally revealed what led to the engagement during an episode of Brown’s popular podcast, Better Tomorrow, explaining that it nearly didn't happen.
According to Woolard, his proposal had been in the works for a couple of months. But the weekend before that was to happen, Brown had spent some time with her family working on a project on their farm in Alabama, which stirred up some emotions and insecurities for her.
She later told Woolard what she experienced and added that her therapist recommended that she not make any big life decisions at the moment, all of which brought up questions about herself. "I was like, 'I don’t even know what love is. Are you sure you want to be with me?' " she recalled, noting that she had no idea this was the week before Woolard planned on popping the question.
That posed a problem for Woolard. “When you were saying this, I was like, 'You've got to be kidding me?' ” he remembered on the podcast. “I was planning on proposing that next Friday. I was like, “Oh my gosh. So I was going through this mental battle adhering to what your therapist wanted you to do and not make any big life decisions. That really stuck with me — ’Well, this is a pretty big life decision,’ So I was like, ‘Do I follow through with my plan or do I preserve her mental health?’ "
After wrestling with what to do for a day, Woolard decided to tell her about his plan. But his confession prompted mixed emotions for Brown, who initially thought it was a joke.
"I understood him not wanting to surprise me so much that it hurt me in any way. But we talked about getting engaged [before], it was coming at some point. All I probably needed was a, 'Hey, we had this big conversation. I am planning to do this somewhat soon.' And that would have been enough prep for me," Brown said. "But then once he told me the date, I was immediately like, 'No, I don’t want to know!' Which I think is fair. That’s the biggest part of it — being surprised!”
Eventually, they decided to postpone the engagement with no pressure. But Woolard wasn’t giving up on surprising Brown.
He contacted his friends Tori and Seth Bolt, who had just given birth to their child. And Seth had the idea of having the engagement on Aug. 24, under the pretense of a baby celebration at Tori’s mother’s property in Hermitage, Tennessee, where she had a farmhouse.
Woolard said in the podcast that he bought a baby gift and hid the engagement ring box underneath the gift inside a bag. On that day, the couple put on some casual clothes and drove to the property. While on the way for the baby celebration, they grabbed Chick-fil-A since Brown hadn’t eaten all day.
As they approached the farmhouse, which Woolard had decorated for the special occasion, Brown recognized a favorite song of theirs that was playing and started to realize what was happening.
“I was so shocked. Definitely didn’t see it coming," Brown recounted to Woolard on the show. "Just like laughing but also being like, 'You got to be kidding me!' "
"I thought I was prepared now, so I could look good every time we went out. And this is the one time that I didn’t think anything was going to happen — that I’m wearing clothes that were on the floor three days old and my hair… so I was freaking out about that," she added.
Woolard took out a three-stone ring and explained its significance as a symbol of keeping God at the center of their relationship. “I got down on one knee and asked you and you said, ‘yes,’ ” he recalled. "And then you started talking about that you just had Chick-fil-A.”
As for the surprise engagement that was supposed to take place at Bolt Farm Tree House the following day, where family and friends were going to attend, Adam said on the podcast that he recorded and edited a video explaining the change in plans that included the previous footage of him getting on one knee to propose to Brown.
The video was later played to the gathering at Bolt Farm, and then afterward, Brown and Woolard walked in to surprise their guests.
“Everything worked out, Woolard recalled on the show.
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Brown and Woolard have been together since they first met in 2021. The couple met on a dating app, and soon into their relationship moved across the country from Los Angeles to Nashville, with their shared dog.
Ahead of their relationship, Brown has brought the public along for her search for love, first appearing as a contestant on Colton Underwood’s season of The Bachelor. Charming the audience and fans, she then became The Bachelorette for the show’s fifteenth season and got engaged Jed Wyatt, though broke up with him after she discovered he had been dishonest with her about having a girlfriend when he went on the show.
Last month, Brown told PEOPLE that her love for Woolard grew as he maintained his “calming presence and big heart.” She shared that he “accepts and loves all versions of me… even the crazy version.”
Woolard, meanwhile, said he admired how his now-fiancée “lives and acts from the truest part of herself despite outside influence."
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