Year In Review: 2020’s Country Music Engagements

Congratulations all these newly-engaged country couples!

Written by Jeremy Chua
Year In Review: 2020’s Country Music Engagements
Photos courtesy of Blake Shelton and Bobby Bones

While 2020 has been a bummer of a year, it has not put a stop on romance in the world—and in the country music community! Some artists like LANCO’s Eric Steedly proposed before the world shut down, while bubbly country singer Abby Anderson got surprised on the boat in a lake during the COVID-19 quarantine lockdown. No pandemic is holding back romance, that’s for sure!

Here’s a look back at 2020’s newly-engaged country singers and couples!

LANCO — LANCO member/guitarist Eric Steedly kicked off the year’s engagements by proposing to his girlfriend, Jessica Wardwell, on Jan. 6. Steedly dropped down to one knee in Mangel Halto, Aruba while the couple were on vacation. On Aug. 23, they became Mr. and Mrs. Steedly!

Drew Baldridge — On Mar. 16, country singer/songwriter Drew Baldridge got down on one knee and popped the question to his longtime girlfriend Katie. “I couldn’t imagine spending the rest of my life with anyone else. Fiancé has a nice 💍 to it 😉,” Baldridge announced on Instagram. The post also featured beautiful photos of their proposal in Palm Beach, Aruba.

Home Free — A real-life proposal in a music video? Check! Home Free’s Adam Chance proposed to his girlfriend Samantha “Sami” Matarantem on Mar. 17, in the video for their rendition of Jason Isbell’s “Cover Me Up.” In the video, Chance belts the song in front of a beautiful sunset while the other members of the a cappella group appear on the side of the screen to deliver vocal harmonies. The couple eventually gets engaged in a romantic backdrop at the end of the video.

Abby Anderson — Despite the bummer of a COVID-19 quarantine, rising country artist Abby Anderson got on a boat to the middle of a lake and…got engaged! In a blissful Instagram post on May 4, the “Make Him Wait” singer announced that she said yes to her longtime boyfriend, Tyler. “TURNS OUT MY MAN CATCHES MORE THAN FISH💍😭,” the caption read. Romantic photos taken from a distance also accompanied the announcement. 

Nick Wayne & Hannah Ellis — Rising country singers Nick Wayne and Hannah Ellis got engaged on Jun. 8, atop a hill at the Tennessee State Capitol. “From next door neighbor, to best friend, to boyfriend, to FIANCÉ! The last 6 years have been the best of my life and I cannot wait for the rest of forever with you, Nick Wayne. ❤️💍,” Ellis wrote on a post, accompanying their romantic engagement photos.

Filmore — Rising country singer Filmore announced on Jun. 15 that he popped the question to his girlfriend Paige! On Oct. 20, just after four months of being engaged, the couple of three years married in a beachside ceremony.

Hailey Whitters — “Ten Year Town” singer Hailey Whitters didn’t have to wait “ten years” to be engaged to her boyfriend of eight years, Jake Gear! Gear popped the question to a surprised Whitters on Jul. 30. “No makeup or bra on, but this guy laid some life on me last night in the field,” Whitters shared on Instagram the next day, accompanied with their simple, blissful selfie.

Jake HootThe Voice season 17 winner Jake Hoot has proposed to his sweetheart, Brittney Hoyt! The singer announced the news on an Instagram post on Sept. 29. “Here’s the big news!! I get to marry my best friend,” Hoot wrote in excitement. “The lyrics God blessed the broken road has never been more true! I’m so glad the God kept bringing us back together time and time again!”

Jameson Rodgers & Sarah Allison Turner— Rising country star Jameson Rodgers is off the market now, ladies! Rodgers popped the question to his 9-year sweetheart and fellow singer Sarah Allison Turner on Sept. 30, at their very first meeting point. “I met @sarahallisonturner at the [The Bluebird Cafe in Nashville] 9 years ago. Took a few years for me to finally ask her out,” the “Some Girls” singer wrote. “Last night I surprised her there and asked her if she’d marry me. She said YES!!”

Bobby Bones — Radio Host, TV personality and stand-up comedian Bobby Bones took to Instagram on Oct. 11 to announce his proposal to his girlfriend, Caitlin Parker. “I am the luckiest. I waited so long for the right one. And it payed off. Surprised her with a secret proposal in the barn in the backyard,” the National Radio Hall of Famer wrote. To make it even sweeter, Bones also surprised Parker with a special performance of Mat Kearney’s “Nothing Left to Lose,” performed live by Mat Kearney himself.

Blake Shelton — Blake Shelton and fellow The Voice judge Gwen Stefani are finally engaged! The couple shared the joyful news on Oct. 27, after 5 years of dating. Accompanying the news was a romantic photo of the superstar couple in a Catholic church. 

Jenny Tolman — Up-and-coming country singer Jenny Tolman is off the market! Tolman and her longtime boyfriend (and producer) Dave Brainard got engaged on Oct. 28 at Jenny Lake, in the Grand Tetons.

Jake Owen — Country hitmaker Jake Owens has popped the question to his longtime girlfriend, Erica Hartlein! The “Made For You” singer shared the exciting news on Nov. 30, with photos of their engagement in a Christmas tree nursery. 5 years ago we went and got our first Christmas Tree 🎄together….at this same spot,” Owens wrote. “This year, I asked her if she’d like to get Christmas Trees 🎄 every year for the rest of our lives.”

Runaway June — Runaway June’s frontwoman Naomi Cooke is off the market, guys! On Dec. 15, Cooke posted a candid photo of herself and her fiancé, Martin Johnson (lead singer of pop-rock band Boys Like Girls), with a simple caption: “By the look of my nails, he surprised me.”

Another Runaway June member is off the market as well! Announcing to fans on Dec. 30, Jennifer Wayne showed off her beautiful new rock and fiancé, Austin Moody. “Happy birthday to the man I get to spend the rest of my life with!!! I love you @theaustinmoody . Can’t wait to celebrate the day with you…,” Wayne said in her Instagram post.

Reba McEntire’s son, Shelby Blackstock — Congratulations are in order for Shelby Blackstock, the only son between country superstar Reba McEntire and her ex-husband, Narvel Blackstock. Like a true dream come true, Shelby posted a photo of him down on one knee in Disneyland, proposing to fiancé Rissa Branch. The race car driver added in the caption, “Closing out the best year of my life the right way- I’m engaged to my best friend!”

Congratulations to all engaged couples!!