Jason Aldean and Brittany Aldean's Relationship Timeline

Controversial meeting

When Jason and Brittany first met, Jason was still married to ex-wife Jessica Ussery, his high-school sweetheart with whom he shares daughters Keeley and Kendyl. Jason was seen kissing Brittany at a Hollywood bar while was still married to Ussery, with the singer apologizing and promising to work on his marriage.

"The truth is that I screwed up. I had too much to drink, let the party get out of hand and acted inappropriately at a bar. I left alone, caught the bus to our next show and that's the end of the story. I ultimately ended up embarrassing my family and myself," he shared on Twitter at the time. "I'm not perfect, and I'm sorry for disappointing you guys. I really appreciate being able to work through this privately with my family and for all your continued support."

Ultimately, Jason and Jessica separated in April 2013 before getting a divorce.

Officially dating

Jason and Brittany announced in March 2014 that they were dating, with the couple taking their relationship public at the CMT Awards that year. When asked by a fan on her Instagram Story this month how she handles her life with "grace and humor," Brittany explained that she had developed a thick skin over the years, likely from the beginning of her relationship with her now-husband.

"When you have heard every negative possible thing you can and called every name in the book...you learn to laugh it off. It's not that serious," she wrote. "My people love me! Nothing else matters in this world."

Engagement

Jason popped the question in September 2014 at the San Diego Zoo around the same time a Billboard interview was released in which the Georgia native expressed his desire for people to stop discussing his controversial personal life. "It has been two years of this s—," he said. "Get over it, already! And then when I finally do get enough of it and say something, every newspaper grabs it. And I'm not trying to get in the headlines — I'm just trying to get people to stop running their mouths."

Destination wedding

The couple tied the knot during a destination wedding in Cancun, Mexico in March 2015, with guests arriving in a secret location ahead of the four-day celebration. For the ceremony, Brittany wore a long-sleeved lace gown by Pnina Tornai, Jason wore a khaki suit and his daughters Keeley and Kendyl added some color to the wedding party with their own custom dresses.

"This is the best day ever!" Jason told Us Weekly of his wedding to Brittany. "I've got my girl here, my friends, my family — it's the best day ever!"

Baby No. 1

The pair welcomed son Memphis in December 2017 after Brittany underwent IVF treatments. "The IVF was probably harder than the actual pregnancy, for me, because it was just such a roller coaster and so difficult," Brittany shared on an episode of the Babes and Babies podcast. "It's such high highs and such low lows, and no one really knows that you're going through it all so you have to just put on a game face and pretend that you're not giving yourself shots in your stomach every day, all day."

She added that doctors would give her a transfer, which was followed by a waiting period to see if the embryo took, an experience Brittany shared she went through multiple times.

"So in your mind, it's almost as though you've had a little bit of a miscarriage, because you expect to be pregnant and then you're not," she said. "And that happened to us multiple times. So then when we finally ended up getting pregnant, it was the most exciting thing ever because we had tried for so long."

Welcoming Navy

In February 2019, Brittany gave birth to the couple's second child together, daughter Navy Rome, with Jason sharing that the pair are officially done having kids. "I'm good. I mean, I think at this point, I mean, this is number four for me, and I got 15, 11, a one year old, and one that's cooking, so to me, four healthy kids, I would feel blessed to have that," he explained at a number one party earlier this year. "I'm good, and my wife's been pregnant for two years, so I don't really think she's in any hurry to jump back and go through that again either, so I think we're good."

So in love

Five years into their marriage, Jason and Brittany are more in love than ever. "He has the ability to be so calm in situations," Brittany gushed about her husband during her Instagram Q&A. "Literally...never raises his voice. Is NEVER disrespectful to me. He is a rugged, manly, southern, a TRUE guy's guy...yet is so lovable. Loves his mama and family more than anything."

"I love waking up with her every day," Jason told Us. "Brittany's energetic and one of those people who sort of flies by the seat of her pants, which I like because I'm a little bit that way, too."