‘Reminders of Him’ star Lainey Wilson reveals financial struggles in upcoming Netflix documentary ‘Lainey Wilson: Keepin’ Country Cool’

Lainey Wilson opened up about the early days of her relationship, revealing she was so strapped for cash when she met her fiancé she had to ask her sister for help.

Wilson reflected on how far she’s come in a clip from her upcoming Netflix documentary, “Lainey Wilson: Keepin’ Country Cool.” The “Reminders of Him” star recalled being “so broke” when she first met her fiancé in 2021 that she turned to her sister for financial support.

After showing off a photo of herself and Devlin “Duck” Hodges on the night they met, Wilson said, “I was broke. I was so broke when we met.

Lainey Wilson revealed she was “so broke” when she met fiancé Duck Hodges in 2021. ( Matt Winkelmeyer/Getty Images for CMT)

“And he thought I was doing a little bit better than I was,” she added. “But a few weeks after we met, my sister had to Venmo me a couple hundred bucks.”

Wilson’s temporary financial setback didn’t seem to deter Hodges, who saw breakthrough success that same year. Wilson and Hodges began dating after meeting and kept things private before making their debut as a couple at the 2023 ACM Awards. Hodges eventually proposed to Wilson in February 2025. The country music star later revealed she was surprised by the former NFL quarterback’s proposal.

“So, I had talked myself into thinking he was going to do it that day,” Wilson said, captured on video by News Channel 5 Nashville. “And then I called my sister. I said, ‘He’s going to propose to me today.’ And she was like, ‘I gotta go.’

“And then I talked myself out of it because I thought, ‘Man, I sure would be upset if I talked myself into this and that don’t happen.’”

Devlin Hodges and Lainey Wilson attend a special screening of “Reminders of Him” March 16. (Jason Davis/Getty Images)

Hodges and Wilson had been planning to visit the George Jones estate, which had been listed by one of Hodges’ friends, a real estate agent. The two made a plan to stop by during the week after this year’s Super Bowl.

“And then, as we [pulled] up, I realized that there were different plans,” Wilson explained. “So, he had it all set up. He had the candles and the picture frames, and it could not have been more perfect.”

Months before their proposal, the “Heart Like a Truck” singer joked she might have to get down on one knee after Bunnie Xo said she hoped Wilson and Hodges get engaged in 2025.

“No pressure, brother! No pressure,” Wilson told Bunnie, who was interviewing the “Watermelon Moonshine” singer for CMT. “I might have to propose to him. We waiting!”

Lainey Wilson and Devlin Hodges got engaged in February 2025. (Terry Wyatt / Getty Images)

Lainey Wilson experienced breakthrough success in 2021. (Brianna Bryson/Wireimage)

Wilson seemingly always knew Hodges was the one for her and revealed she actually sent him engagement ring choices four years ago.

“Honestly, as a joke, right when we first started dating, because we knew pretty much immediately, we were like, ‘OK, we’re gonna be in each other’s lives.’ It just felt that natural. And as a joke, I had texted him some big rings, being like this is what I like. He was like, ‘Oh, Lord, I better start saving now,’” she recalled in the video captured by News Channel 5 Nashville.

“We’ve been together for four years. What he did is he went in and designed it and kind of put some of those rings together that I sent him. So, I’d have said yes if it was a tiny little thing. But he messed up.”