Michael O' Shields and Dolly Vaughn

A Woodruff man proposed marriage in a unique and timely way over the weekend. 

Woodruff High School graduate Michael O’Shields Jr. had spent the better part of three months trying to come up with a light-hearted way to propose to his girlfriend Dolly Vaughn, also a Woodruff High grad. Finally a suggestion from his mother stuck – “Why don’t you carve it into a pumpkin?” she asked. Being unique and timely, he knew it was the perfect solution.

O’Shields waited until Vaughn’s family had gathered to carve pumpkins, part of a tradition they take part in every year. As everyone began work on their orange colored creations, he told them “I’m going out to the backyard to work on mine”, which struck the family as a bit odd.

“We didn’t know what he was up to” Vaughn said. “My sister and I kept trying to get a peek out the back window to see what he was doing.” 

Michael O' Shields and Dolly VaughnWith his whittling finished and everything set up, he lit a candle to put inside, and called everyone to the backyard. “I’m finished, come out back and see my pumpkin” he told the family. After Vaughn saw the pumpkin, O’Shields got down on one knee and presented the ring he had been keeping secret for 6 months. She replied with a resounding “Of course!”

“I couldn’t have been more surprised, or happier” Vaughn said. “I had no idea he had already bought a ring and was planning to ask me to marry him.”

O’Shields and Vaughn met for the first time nearly 8 years ago at West End Baptist Church while they were both in middle school. Vaughn thought he was cute and for years her sister tried to get them to meet. Finally, when O’Shields was in 11th grade at Woodruff High, his locker was located adjacent to Vaughn’s sister. The sisters swapped lockers to bring them closer together. “The first thing he ever said to me was something about a math test as he closed his locker and headed to class” Vaughn recalled. Within about three months, they went on their first date.

The couple have yet to set a date and begin planning for their wedding.

O’Shields stated it took “about twenty minutes” to carve out the big question. 8 years of acquaintance, 3 years of dating, 6 months of planning, and 20 minutes of carving all led up to a relationship that will last a lifetime.



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