Lainey Wilson’s Toughest Time? ‘Dating a Boy Who Got a Girl Pregnant’

Lainey Wilson may be at an all-time career high now, but it hasn’t always been that way.

In a new episode on the Artist Friendly podcast, hosted by Good Charlotte star Joel Madden, the singer talks about some of the personal and professional hurdles she hit early on in her career.

Wilson describes an ebb and flow of success during her early days in Nashville, saying that just as she started to hit some momentum, something would come along to knock her down.

“I felt like, ‘Okay, I’ve got something going, it’s cooking.’ And then it kinda gets taken away,” she recounts, “And I have to kind of start over and switch gears and find a different way.”

Specifically, she remembers a time soon after she arrived in Nashville.

Fans already know that when Wilson first got to Music City, she lived in her camper as she started her career. What they might not know, though, is that she had a mentor during this time named Jerry Cupit, a producer and songwriter who hailed from the same hometown as Wilson: Baskin, La.

Cupit had a connection to Wilson’s family: In the ’70s, her grandfather gave Cupit some money to support his dreams of moving to Nashville and working in the music industry. Cupit never forgot the kindness, and he supported Wilson when she herself was a budding musician, helping her learn to write songs as a kid and later allowing her to park her. camper in the parking lot of his studio.

“I was living in my camper, [and] he and I, we wrote music together every single day for three years,” Wilson recounts.

In 2014, Cupit unexpectedly died.

“It was a shock to everybody and I had to start over from square one,” Wilson says. “… That was definitely, like, a dark time in my life. Because when you write 300+ songs with somebody, you become really close.”

That wasn’t the only earth-shattering event that happened in Wilson’s life around this time.

“I was dating a boy who got a girl pregnant. And it was all happening at the same time,” she says. “I was like, ‘When it rains, it pours.'”

Amid her feelings of grief and betrayal, Wilson says she learned to “embrace the heartbreak,” a lesson that sticks with her to this day.

“Because I’m like, ‘Is this happening to me? Am I getting punked? Is it happening just so I can have something to write about?'” she wondered. “But into now, I’m just learning how to adjust with my life changing.”

That attitude has served her well, helping her create hard-hitting songs like “Heart Like a Truck” and propelling her to the top of her game.

Most recently, Wilson is a country music superstar with a growing catalog of awards and accolades, and she recently won CMA Female Vocalist of the Year for the third year running.