Hannah Brown and Adam Woolard's Relationship Timeline
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From meeting on a dating app to getting engaged, here’s everything to know about Hannah Brown and Adam Woolard’s relationship
Hannah Brown and Adam Woolard are engaged!
On Aug. 24, 2023, Woolard popped the question to Brown in front of friends and family at a farm in Whitwell, Tennessee.
“(I loved) not only the intimacy of the surprise by ourselves, but also how we were able to celebrate with friends and family. And the surprise. I love surprises,” Brown said.
The bride-to-be and Woolard first met on a dating app after she famously went looking for love on both The Bachelor and The Bachelorette.
In January 2021, just two months after sharing with her YouTube viewers that she was "putting [herself] out there" and dating again for the first time since her season of The Bachelorette wrapped in 2019, the Alabama native was spotted holding hands in Los Angeles with Woolard. The couple publicly confirmed their relationship on Valentine's Day in 2021.
Brown and Woolard have shared plenty of sweet moments since then and have taken some major steps in their relationship, including moving in together, becoming dog parents — and most recently — becoming engaged!
Related: Hannah Brown's Boyfriend Adam Woolard Proposes to Her in Jordan Davis' New Music Video
From their Instagram debut to their engagement, here is a complete timeline of Hannah Brown and Adam Woolard's relationship.
January 23, 2021: Hannah Brown and Adam Woolard are first linked
In January 2021, Brown and Woolard were seen enjoying a stroll together down Abbot Kinney Boulevard in Venice Beach, California. The pair were holding hands and casually dressed in similar army green jackets and face masks for the outing, which sparked dating rumors.
A few weeks later, Brown's ex Tyler Cameron, whom she dated on The Bachelorette and remained friendly with, weighed in on Brown's new romance. "I haven't met him but seen pictures of him. Good looking guy, so I'm happy for her," Cameron said of Woolard to Entertainment Tonight.
February 14, 2021: Hannah Brown and Adam Woolard celebrate Valentine's Day
Brown and Woolard publicly confirmed their relationship for the first time on Valentine's Day in 2021. She posted a sweet photo on Instagram, showing her and Woolard kissing while riding horses. "Happy Valentine's Day @admandew ❤️," she wrote in the caption.
February 19, 2021: Hannah Brown and Adam Woolard star in a music video
The former Bachelorette starred in country artist Jordan Davis' "Almost Maybes" music video, which chronicles the ups and downs of finding true love. In the video, the singer experiences a series of bad dates and relationships before realizing he's found his "one" — played by the Dancing with the Stars winner. In a surprise twist, Woolard makes a quick cameo in the video and can be seen proposing to Brown.
March 3, 2021: Hannah Brown talks about her first date with Adam Woolard
In a candid Q&A posted to her YouTube channel, Brown answered a series of fan-submitted questions about her new relationship. In the video, she revealed that they met on a dating app and that she "liked his photo first," but it was Woolard who made "an actual move that made any ruckus."
Woolard did not appear in the video, but he did write down his answers, which Brown read out loud. One fan asked what Woolard's first impression of Brown was. "Effortlessly beautiful and vibrant and a little frantic, but so beautiful. Instant spark," Woolard wrote. With a blush, Brown confirmed that "there definitely was a nice spark."
March 29, 2021: Adam Woolard shares a beachy photo with Hannah Brown
For Brown's second appearance on Woolard's Instagram feed, he posted a picturesque snap of the pair enjoying a windy beach day.
Along with the picture, he added the caption: "Life tends to assume a flow state when values and purpose are aligned 💙💫."
May 7, 2021: Adam Woolard supports Hannah Brown's clothing collaboration
In honor of his girlfriend's collaboration with clothing brand Show Me Your Mumu, Woolard shared a sweet picture of the couple going in for a kiss.
"Many have seen you shine on TV, but few get to see how hard you work ... how thoughtful you are ... and how you care for others ... every single day 😎," Woolard captioned the photo. "Cannot wait for this collab to drop!! @hannahbrown x @showmeyourmumu - the perfect match. #may16."
May 12, 2021: Hannah Brown and Adam Woolard play "Never Have I Ever"
In a fun video posted on Brown's YouTube channel, the couple played a game of "Never Have I Ever" together and revealed whose DMs they've slid into.
"It's usually girls that I'm like, obsessed with. Like Taylor Swift," Brown said. "Oh my God, if she saw the messages. I had to go back and like, take away some of my messages I sent her."
Woolard shared that he had sent a message to Billie Eilish after watching a video of Post Malone and Jimmy Fallon going to Olive Garden. "And I saw a video of Billie Eilish and was like, 'She seems so cool.' I just wanted to get to know her and take her to Olive Garden. But I think I said Red Lobster, that I wanted to take her to Red Lobster."
He continued, "I deleted it the next day. But I was like, 'Billie, I just think you're the coolest chick. I want to take you to Red Lobster.' And that was it."
May 16, 2021: Hannah Brown wishes Adam Woolard a happy birthday
The Bachelorette alum celebrated Woolard's 31st birthday with a sweet tribute on Instagram. "Happy Birthday, @admandew. It's so fun celebrating you!" Brown captioned a video mashup of the pair sharing kisses and showing off their dance moves.
"You radiate goodness, positivity, and joy. I'm so thankful to be surrounded by your shine. You're my sweetie💙. Let's keep dancing, k?" she added.
July 25, 2021: Hannah Brown and Adam Woolard enjoy tacos with Matt James
Brown enjoyed an evening of tacos and quality time with her "favorite guys" — boyfriend Woolard and former Bachelor Matt James, who previously gave Brown and Woolard's relationship his stamp of approval.
"Love a good taco and tv night with my favorite guys!" Brown wrote on her Instagram Story. Brown shared a second photo from the night, smiling with James on the couch, and captioned it, "Missed you. Thankful for you. Here for you. Proud of you. @mattjames919."
September 24, 2021: Adam Woolard wishes Hannah Brown a happy 27th birthday
In honor of Brown's 27th birthday, Woolard posted a video montage of the pair's moments together and added a touching caption.
"OH THAT SMILE. It illuminates everything around it," he wrote. "Happy birthday, Sweetie!! If you're smiling, it's because of YOU. You've created such an amazing life … so happy to be a part of it. Excited for what this next year will bring 💙."
November 18, 2021: Hannah Brown opens up about her relationship with Adam Woolard
Ahead of the release of her memoir, God Bless This Mess: Learning to Live and Love Through Life's Best (and Worst) Moments, Brown sat down with PEOPLE to discuss the book and how writing it helped her "heal" from her past hardships — romantic and personal. She also opened up about her newfound happiness with Woolard and revealed what initially attracted her to him.
"He knows himself and I think that's the biggest thing," she shared. "He's very confident in what he deserves and what he wants to give someone else. He's genuine and he's truly one of the best humans I've ever met. And he is so cute!"
Brown continued, "I have a lot of energy and he is so calm. I think he's entertained by my frazzleness!"
"I've always longed for safety in relationships but I've put myself in unsafe positions," added the first-time author. "Adam keeps showing up. And he always makes me feel so safe."
November 23, 2021: Adam Woolard promotes Hannah Brown's book
Woolard was all smiles as he showed off his current read on Instagram — his girlfriend's then-newly released memoir, God Bless This Mess.
"GOD BLESS THIS MESS IS OUT TODAY!!!" Woolard captioned the photo. "So proud of you @hannahbrown … I saw the grind firsthand. You deserve it all 😎."
December 11, 2021: Hannah Brown and Adam Woolard spend a weekend in New York City
The couple headed to New York City for a romantic holiday weekend. Brown shared three photos on Instagram that showed the pair ice skating at Rockefeller Center and enjoying views from Top of the Rock. "On the rocks, please! 🎄🥂⛸," Brown captioned the snaps.
December 29, 2021: Adam Woolard and Hannah Brown celebrate the holidays in matching pajamas
Brown shared photos of her Christmas gathering on Instagram, including one of her and Woolard in matching green-and-white striped pajamas. Brown's family and friends were also at the holiday get-together.
January 22, 2022: Hannah Brown and Adam Woolard welcome home a puppy
The couple took a major step in their relationship together, becoming parents to an Australian labradoodle puppy named Wally. Brown made her dog mom status Instagram official with photos of herself picking her new best friend up at the airport. "Wally Meets World," Brown captioned her carousel of photos.
"Welcome home little buddy," Woolard wrote on his own Instagram post, which Brown commented on, saying, "So glad you're my doggie's daddy."
February 14, 2022: Hannah Brown shares what she loves about Adam Woolard
For their second Valentine's Day together, Brown shared a sweet video montage detailing some of the things she loves about Woolard, including "his sick dance moves" and "his snuggles."
In her caption, Brown wrote, "I think it is so important to recognize and celebrate the seemingly minuscule attributes of our partners that mean so much, but are often taken for granted. What makes a relationship work is often not expensive gifts and insta-worthy events. It's the simple. It's the silly. It's the little moments that remind you why you choose to love that person every day."
Brown continued, "To my sweetie, Happy Valentine's Day. I'm so grateful for how you love me. Thank you all the little moments! 😘."
April 29, 2022: Hannah Brown speaks about "mature" relationship with Adam Woolard
During an appearance on the Tamron Hall Show, Brown opened up about using alcohol as a coping mechanism after her time on The Bachelorette and Dancing with the Stars.
"I'd never really been a drinker before and I was on TV like every Monday for an entire year and didn't know how to handle how my life had so publicly been displayed," she explained.
Brown shared that she is in a much better place today, due in part to her healthy relationship with Woolard. "I'm so thankful for my relationship now. It's such a mature relationship of two people who have gone on different journeys," she said. "I think I had to go through that journey of asking this question of 'Who am I?' and 'What do I want?' and he's also gone on that journey too."
May 11, 2022: Hannah Brown and Adam Woolard move in together
Brown and Woolard took another big step in their relationship and moved in together. The couple gave PEOPLE an exclusive tour of their apartment in Santa Monica, California, which they decorated with the help of design group Pure Salt Interiors.
"We both wanted something warm and inviting, comfortable and coastal. We wanted this apartment to feel like home for whoever walks through the front door," Brown told PEOPLE. "Every seat in the apartment is cozy and the design goes perfectly with the natural environment here in Santa Monica."
June 2022: Hannah Brown and Adam Woolard vacation in Europe
In June 2022, Brown and Woolard traveled to Italy and France. While in France, the couple visited Nice, Aix-en-Provence and Versailles.
"Provence and @admandew, they both stole my heart," Brown captioned photos and a video of her and Woolard at La Villa Gallici – Relais & Château in Aix-en-Provence.
After returning home from their European getaway, however, Brown revealed on her Instagram Story that the pair had tested positive for COVID-19. "Ugh. It got us," she wrote over a photo of the two cuddling in bed.
September 24, 2022: Adam Woolard wishes Hannah Brown a happy 28th birthday
Woolard celebrated Brown's birthday with an adorable video montage of the two. "Who else has front row tickets to the HB show every year?" he wrote in the Instagram caption. "Witnessing you experience new places is one of my favorite things. Cannot wait to create more memories with you.
He finished the post with a simple "Happy birthday, Sweetie," plus a blue heart emoji.
October 17, 2022: Hannah Brown and Adam Woolard attend the Ticket to Paradise premiere
Brown posted pictures on Instagram of her and Woolard on the red carpet at the Ticket to Paradise premiere. In the snaps, the two stood close and smiled, with Woolard's arm wrapped around Brown's waist. They wore coordinating outfits, too: the Bachelor alum wore a black-and-white gown while Woolard was seen in a white coat and black pants.
Brown captioned the photos with "a fun night at the movies 🎞🍿😍."
March 2, 2023: Hannah Brown says her relationship with Adam Woolard has been "so easy"
Brown spoke to PEOPLE about making it to the finale on Fox's reality series Special Forces: World's Toughest Test, praising Woolard for his support along the way. "He was like, 'This is so badass,' " the former Bachelorette star said of her boyfriend.
Brown also said she's "excited" about the couple's future plans to move to Nashville and noted that "everything with us has been so easy."
"He's helpful, he cleans, cooks, does everything," she said of Woolard. "He checks off things I didn't even know I wanted. And he's my partner in everything."
May 16, 2023: Hannah Brown celebrates Adam Woolard's 33rd birthday
Hannah Brown Instagram
In honor of his birthday, Brown gave Woolard a special shout-out on Instagram.
"Happy Birthday to my favorite person, the best dog dad, and the hunk that is kinder than he is good-looking (i know, it’s wild!)," she captioned a carousel of photos with her beau. "I love doing life with you. You really are the best person I know and I’m the luckiest girl to be loved by you!"
August 2, 2023: Hannah Brown talks about meeting Adam Woolard on a dating app
In an episode of her Better Tomorrow podcast, Brown recalled how she and Woolard met on a dating app.
"I had great luck on a dating app. I was only on it for, like, maybe a little over a week and met Adam," she said. "It was, like, maybe two weeks."
She added, "We are madly in love and we just have a good time together."
August 24, 2023: Hannah Brown and Adam Woolard get engaged
Bonnie McGhee
Woolard popped the question to Brown in front of friends and family at Bolt Farm Treehouse in Whitwell, Tennessee.
Brown originally thought she and Woolard were going to the farm to visit their friends Seth and Tori Bolt, but instead, Woolard had organized a romantic proposal complete with candles and red rose petals.
“I feel like I have been so busy with putting roots down in our new city Nashville and starting my new podcast I hadn’t really thought about it much so if he did slip as he was planning, I did not catch on,” Brown told PEOPLE. “We had talked about getting engaged, but I felt so content and safe in our relationship, I wasn’t rushing it.”
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