Inside Country Singer Dillon Carmichael's Romantic Proposal to His Girlfriend Shayla Whitson

Annette Shadeya
Feb 11, 2021
09:15 A.M.

Country singer Dillion Carmichael is officially off the market after dishing details of his romantic proposal to his girlfriend of two years, Shayla Whitson, on Saturday after popping the big question.


Dillion Carmichael surprised his now fiance Shayla Whitson, using their second-anniversary photo shoot to ask for her hand-in-marriage, where she did not hesitate to yes as soon as he got down on one knee.

Decorated with petals, the couple shared their intimate moment at the beautiful grounds of Whitewood Hollow, where Carmichael admitted he was a bundle of nerves and barely remembers anything from that point.


Secretly planning the engagement, the country singer thought Whitson was briefly onto him when he excluded her on a trip to Kentucky. He used to ask her parents for permission for their daughter's hand in marriage.

The pair revealed wedding bells should, however, not be ringing soon as they are aiming for a long engagement of almost two years due to having goals they would both like to meet before tying the knot.

“We have made a commitment to each other, and now we can just take our time.”


After being enamored by her appearance in 2017 during his concert in Kentucky, Carmichael shares he instantly knew Whitson would be his future wife before the pair began dating and even making jokes about it.

The country singer admitted he was feeling shy, and it was Whitson who made the first move by approaching him in conversation. Since then, Carmichael ensured Whitson's name topped every guest list for his concerts.

Carmichael spent thousands of dollars to lose weight.


After the couple began to date, their unique bond drove Carmichael to release a single titled “I do for you” in 2019, which came as a surprise to fans since it was rare for the singer to release romantic love songs.

The country singer revealed he went on to enlist Whitson's help to feature in the music video. The song had a special meaning of a man deeply infatuated in love who would do just about anything for his partner.

"Making this lyric video was so special to me! I got to make so many great memories with my beautiful Shayla."


Carmichael came from a family full of talented people such as his mother Becky Montgomery, vocalist for the 90’s “Montgomery Family Band,” which featured her brothers, but the singer strived to make a name for himself.

Before making it big in the industry, Carmichael recalled a difficult conversation with his friend Luke Combs questioning if they were ever going to secure a record deal due to being plus-sized.

Back then, the industry-standard favored slimmer men. As a result, Carmichael spent thousands of dollars to lose weight, even starving himself in hopes of becoming smaller, though he didn’t see any results.

Fortunately, his following judged the country singer on his music and not his physique. Carmichael, who has now made a name for himself, joins a

of celebrity couples who’ve gotten engaged in 2021.

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