Cole and Molly met for the first time in Nashville, TN. Molly was visiting while on spring break with her best friend, Jamie Rayhart. Cole was performing on the rooftop stage of Tootsies, on Broadway Nashville. Molly and Jamie sat and listened to Cole and his band sing for a little while. When Cole sang the song "Tennessee Whiskey" Molly jokingly said to Jamie, "He's CUTE! I'm gonna marry him one day". Molly later went up to Cole and the two exchanged phone numbers. Molly and Jamie met up with Cole and his best friend, Landon later that night. Cole was a perfect gentleman and made sure the two girls were safe all night and that they got back to their hotel without any issues. Fast forward 4 years, and Jamie was helping Cole plan the perfect proposal!

Cole proposed to Molly in Gatlinburg, TN in April 2024. He picked out a beautiful air bnb and coordinated every detail with her best friend, Jamie. Jamie and her husband, Tommy planned to drive all the way from their home in Pennsylvania to be part of this. It was going to be the perfect proposal & romantic couples weekend..... until Cole and Molly's puppy Lyla had other ideas. Three days before the trip, Lyla learned how to jump up on the bar stools and climb onto the counter. Lyla ingested Molly's medication- that of which is toxic to dogs. Cole and Molly drove her to the emergency vet, where Lyla stayed in the animal ICU for 3 days. Fortunately, she was okay and was discharged just in time for the trip. The only problem is that she needed follow up medical care to ensure she was healthy and had no long term complications. Which meant, Lyla was coming to Gatlinburg. Instead of the lovely brunch Cole had planned, he and Molly ended up in a vets office in Pigeon Forge, TN. At this point, everyone was over it and Molly never imagined she'd be getting engaged 24 hours later. Thankfully Lyla got a good report and they could finally enjoy their trip. While Molly, Cole and Lyla went to the store to grab some things to grill out for dinner, Jamie and Tommy were setting up the balcony with candles, rose petals and photos of Cole and Molly over the years. When the couple got back to the air bnb, Cole ran upstairs to "check on something" and Jamie asked Molly if she wanted to have a glass of wine on the rocking chairs on the balcony. The two went upstairs and Cole was waiting on the balcony with the ring! Even though Lyla threw a wrench in the plans, she really added to the element of surprise!