Lainey Wilson has revealed that she was so financially strained early in her career that she had to rely on her sister for money, even as her music began gaining radio play.
In a clip from her Netflix documentary Keepin’ Country Cool, Wilson reflects on meeting her now-fiancé, Devlin “Duck” Hodges.
“I was broke. I was so broke when we met,” she said. “And he thought I was doing a little bit better than I was. But a few weeks after we met, my sister had to Venmo me a couple hundred bucks.”
At the time, Wilson had already released Things a Man Oughta Know to radio in August 2020. The song’s commercial success took several months to gain traction with radio and streaming audiences. It eventually reached No. 1 on Billboard’s Country Airplay chart in September 2021, though artists typically wait months longer to receive royalties.
Wilson’s comments highlight the financial uncertainty she faced during her rise to fame. The documentary describes this period as “her struggles and triumphs at a pivotal career moment.”
In the clip, Wilson also discussed her love of songwriting.
“I knew whenever I had written my first song that I loved how it made me feel when I was in the middle of writing the song,” she said. “When I was coming up with the idea, feeling like, ‘Man, I created something from nothing. How cool is that?’”
She added, “And I knew that that feeling was so special that I couldn’t completely let it go, and I think that’s why I knew it was my calling.”
Wilson’s relationship with Hodges developed during this time. The couple began dating in 2021 after meeting through mutual friends and later became engaged in February 2025.
Wilson described their first date at a bar called Silverado’s, noting its affordability.
“It had free beer and wine from 5 to 10 p.m.,” she said during an interview. “I was like, ‘This boy likes to ball on a budget, too. This is gonna work out!’”
Wilson stated that wedding planning is ongoing but not rushed. At an event promoting her film Reminders of Him, she said, “Girl, I need some help. I need some help,” before adding, “It’s going good. Honestly, we’re taking our time, and I’ve told him, and he’s on the same page.”
She emphasized that they want their wedding to be “about what it’s supposed to be about and just enjoy it.”
