Luke Bryan and Caroline Bryan have been married since 2006 and share two sons

Luke Bryan and Caroline Bryan’s relationship has gone the distance.

The pair met in college in the late ’90s and dated on and off for a few years before getting married in 2006. They went on to welcome two sons: Thomas “Bo” Boyer and Tatum “Tate” Christopher. They also helped raise Luke’s nieces and nephew after the deaths of his sister, Kelly, and his brother-in-law.

Caroline has been by her husband’s side for all of his biggest career moments; she even supported the couple financially before Luke’s career took off.

“My life is truly everything I could have dreamed it would be,” he told PEOPLE in October 2013. Eventually, though, he dreams of settling down with Caroline and his kids on his farm. “Rocking on a porch swing when I’m 75, with Caroline and with a yard full of grandkids,” he once said. “That’s a big ol’ fulfilled life for me.”

From their college days to their hardships, here is a complete timeline of Luke Bryan and Caroline Bryan’s relationship.

Fall 1998: Luke Bryan and Caroline Bryan meet in college

Luke and Caroline met when they were both students at Georgia Southern University. She was a freshman, and he was a senior.

“We met in college back in fall 1998. At a little bar called Dingus MaGee’s in Statesboro, Georgia,” Luke told HuffPost in 2012. He also told The Boot that, for him, it was love at first sight. “It took me eight seconds to figure it out and it took her about eight years to figure it out,” he admitted. “I had to drink a lot before I could go talk to her, but I did. Somehow I managed to ease over there and somewhat be charming. It was one of those situations for me, it was like, ‘Who is that and how do I go talk to her? And, yep, I’m going to marry that girl.’ ”

Although Luke may have known right away, Caroline told PEOPLE he still took it slow. “We hung out as friends first and he never made a move on me,” she said. “I kissed him first! He was always so scared of making a girl feel uncomfortable, he wouldn’t cross a line.”

Early 2000s: Luke Bryan and Caroline Bryan date on and off

After meeting, the couple dated on and off before breaking up for a longer period once Luke graduated college in 1999.

“We’d date a little in college, and then we’d break up,” Luke told Kellie Pickler and Ben Aaron during a November 2018 episode of Pickler & Ben. “And then I would be devastated. We’d get back together, break up. Then she would be devastated.”

Luke and Caroline’s “dark ages” following his graduation, actually turned out to be beneficial for the pair.

“We were apart for 5½ years, which was kind of a blessing because I went off to Nashville, got all this going,” he explained of his music career. “She finished college. She went and actually had a career.”

2004: Luke Bryan and Caroline Bryan reunite and get engaged

Following their time apart, Luke and Caroline reunited in the same town where they had first met. “I was playing a little bar in Statesboro and she just happened to kinda be in town,” he told HuffPost. “We kinda saw each other and talked a little bit and then started emailing back and forth a little bit. And she was like, ‘Hey, you want to come to my family’s Christmas party?’ I went to the party and the rest is history.”

This time around, the pair were determined to stay together. Luke proposed to Caroline in front of Nashville’s Parthenon replica.

December 8, 2006: Luke Bryan and Caroline Bryan get married

The couple got married in December 2006 in the Turks and Caicos Islands. They then headed to the Colorado mountains for their honeymoon.

Luke has said that Caroline kept them afloat financially in the early days of their marriage before his career took off. “When we got married, her career supported me when I was making about $10,000 a year,” he said. “She was the one bringing in the dough.”

March 18, 2008: Luke Bryan and Caroline Bryan welcome their first son

Luke and Caroline became welcomed their first child together on March 18, 2008, in Nashville. The new dad said he was “over the moon” to meet Thomas “Bo” Boyer Bryan, adding, “Everyone is doing great! My fishing buddy is finally here!”

“I thought being on stage was an amazing feeling, but there is nothing that can top watching my wife bring our son into this world,” Luke told PEOPLE. “There is no way I would have missed this for anything.”

2009: Luke Bryan and Caroline Bryan have a miscarriage

Following the birth of Bo, Caroline suffered a miscarriage. “When [Bo] was born, he was a surprise,” Caroline later said during a 2019 episode of Get Real with Caroline Hobby. “I got pregnant when we had been married for six months. I was not expecting that at all, and then we had a miscarriage.”

“I knew it wasn’t my fault,” she continued, adding that Luke “didn’t really know how to comfort” her. “He just didn’t get it, but as girls, when you go through it and you lose it, there is a loss and it sucks and it hurts.”

August 11, 2010: Luke Bryan and Caroline Bryan welcome their second son

Almost two years after welcoming Bo, Luke and Caroline announced that they were expecting another 𝚋𝚊𝚋𝚢. Their second son, Tatum Christopher, was born on Aug. 11, 2010, in Nashville. “All I ever hoped for was one boy and to have two, it’s going to be fun,” Luke told PEOPLE. “I’ve already got new fishing spots picked out for us.”

Luke was picking up a treat from Sonic for Caroline when Baby Tatum arrived earlier than expected, so the star hadn’t fully prepared for the occasion. “I had planned to buy her a little present today but then the 𝚋𝚊𝚋𝚢 came early, so the slushie will have to do it for now,” he said.

2014: Luke Bryan and Caroline Bryan take in their nieces and nephew

In 2014, Luke’s brother-in-law, Ben Lee Cheshire, died at the age of 46 of a heart attack. Seven years earlier, Luke had lost his sister Kelly, Cheshire’s wife, of undisclosed causes. Kelly and Ben were survived by their three children: daughters Kris and Jordan and son Tilden. Til came to live with the Bryans, and while the girls didn’t live with the couple full-time, Caroline and Luke took an active role in raising them. “We never thought twice about it,” Caroline once said.

In 2015, the singer talked to PEOPLE about raising his nieces and nephew. “You don’t want to sound like you love having them so much that you’re glad it’s the situation, but we’re honored to be doing what we feel was the right thing,” he shared.

Luke later told PEOPLE: “Obviously my nieces and nephew, they didn’t ask for this. Their life was amazing before Caroline and I took a more prominent role, even after losing their mother. Now my focus is trying to do what we can to help them.”

August 25, 2015: Luke Bryan reveals Caroline Bryan inspired the song “Strip It Down”

When it comes to his songwriting process, the country artist has said that his wife has often served as his muse.

“Yes, Caroline is definitely an inspiration behind the song — it’s just 𝓈ℯ𝓍y to be thinking about her when I’m writing,” Luke told PEOPLE of his 2015 single “Strip It Down.”

“This song feels like new territory for me,” he added. “It’s fun putting songs out you know people are going to be slow dancing or falling in love to.”

December 8, 2016: Luke Bryan upgrades Caroline Bryan’s engagement ring

In December 2016, Luke and Caroline celebrated their 10th wedding anniversary. In honor of the milestone, the singer upgraded his wife’s engagement ring with a new diamond. After Caroline was spotted wearing the impressive piece of jewelry at the CMT Artists of the Year event in Nashville, Luke later told PEOPLE, “Oh yeah, I came with that one right out the gate.”

“It was a little 10-year anniversary gift. Ten years with me feels like a thousand,” he joked. “It was certainly the least I could do!”

July 17, 2019: Caroline Bryan celebrates Luke Bryan’s birthday

Caroline helped Luke celebrate his 43rd birthday by posting a poem on Instagram. “Roses are red, violets are pleasant, you have everything … so you get no present!” she wrote alongside a series of photos of the country crooner. “Happy birthday Love Bug!!! I love you to the moon and back. Here’s to another year of completely random, classy pictures.”

December 8, 2020: Luke Bryan and Caroline Bryan celebrate their 14th anniversary

Luke and Caroline celebrated their 14th wedding anniversary in December 2020, each posting sweet throwback photos to mark the occasion. “Happy 14th anniversary my love. What a ride it has been. I love you so much. We be looking young in this one. I love you,” Luke captioned a photo from their wedding day.

Caroline shared a series of photos on her page and wrote, “Marriage … being with the one person you get to annoy for the rest of your life. Luke, you are one brave man! Happy 14th anniversary love bug!”

February 14, 2021: Luke Bryan shares what makes his and Caroline Bryan’s marriage work

Amidst the COVID-19 pandemic, Luke spoke about what makes his and Caroline’s 14-year marriage work. “Obviously quarantine has certainly put its share of new things to navigate,” he told PEOPLE in February 2021.

“Caroline and I are used to spending quite a bit of time apart, and now I’m just here every day,” he continued. “But the main thing with us is properly inserting alcohol in parts of the relationship — it does a really, really good job for us. I’m playing!”

He added, “It’s all about communication and giving each other time to go do the things that we’re passionate about.”

October 20, 2021: Caroline Bryan says Luke Bryan’s “ass-shaking” has provided for them

Luke may be known for his music, but his fans also know him for his fun and suggestive stage presence. During an appearance on Jay Cutler’s podcast, Caroline was asked how she feels about her husband’s status as a 𝓈ℯ𝓍 symbol. “I’m used to it. I don’t think about it,” she said.

“Luke’s ass and his ass-shaking has made us a lot of money … I’m not worried about it. It comes with the territory. As long as [fans] are respectful, then whatever,” she added. As for what’s respectful, Caroline said, “Don’t touch, don’t grab.”

December 8, 2021: Luke Bryan and Caroline Bryan celebrate their 15th anniversary

2021 marked 15 years of marriage for Luke and Caroline. Luke shared a photo of himself and his wife on Instagram and wrote, “Happy 15 Anniversary to my love. Don’t know how you put up with my goofy ass. I love you to the moon and back.” Caroline joked about their busy schedules, commenting, “Happy 15th! Maybe we’ll see each other at some point today! Love you!”

Caroline shared a similar sentiment on her Instagram Story. Along with a photo of herself drinking a mimosa, she wrote, “Sorry our schedules are the complete opposite. We will celebrate soon. Until then … Happy 15th anniversary @lukebryan.”

February 2022: Luke Bryan opens up about balancing work and family life with Caroline Bryan

Luke spoke to PEOPLE in February 2022 about his new tour and his Las Vegas residency. He also talked about his wife and sons, saying, “The boys have a good understanding that so many of the amazing things that they get to do in life is all about the sacrifices that me and Caroline have to make.”

“It’s just having a nice balance,” he said.

February 14, 2022: Caroline Bryan shares a Valentine’s Day message for Luke Bryan

On Valentine’s Day 2022, Caroline posted a message for her husband on Instagram. She included a photo of the pair embracing in a field while she was sitting on a wooden fence. “I’ll get a splinter in my butt any day for you! Happy Valentine’s Day @lukebryan ❤️ #forevervalentine,” she wrote.

“God. I’ve never seen this pic,” Luke commented. “So pretty. Happy valentines my love. I love you.”

December 8, 2022: Luke Bryan and Caroline Bryan celebrate their “sweet 16” anniversary

In December 2022, Luke and Caroline celebrated their “sweet 16” wedding anniversary by sharing posts on Instagram.

Luke went for humor, posting a photo of himself sporting a mullet wig alongside his wife in a shiny visor. “Happy 16th anniversary love. It is so amazing sharing this life with you. Thank you for putting up with all my craziness I throw your way,” he captioned his post in part.

Caroline at first seemed to take things a bit more seriously by posting a video montage of her and Luke set to Barry White’s song “You’re the First, the Last, My Everything” — though the video included several costume photos, too.

“Sweet 16!!!! Happy anniversary Love Bug…16 years ago we had zero clue what we were stepping into. The good, the bad, silly moments and stupid arguments. It’s been worth it all and I love you more every year! ❤️ @lukebryan,” the caption read.

July 17, 2023: Caroline Bryan celebrates Luke Bryan’s 47th birthday

In honor of her husband’s birthday, Caroline penned a sweet post about Luke on Instagram.

“Happy birthday to my love bug!” she captioned a series of photos and videos of the country singer. “Whether we like it or not, you give us an adventure every single day! We love you to the moon and back.”

December 8, 2023: Luke Bryan and Caroline Bryan celebrate 17 years of marriage

The couple marked their 17th wedding anniversary with posts on Instagram.

“Pretty impressive how we’ve managed to tolerate each other for so long!!! I love you!” Caroline captioned a photo montage. Bryan created his first Reel for the occasion and wrote, “Happy 17 years together love. I love you.”