Jenna & Bailey

Jenna & Bailey

September 21, 2024 • Watertown, SD
Jenna & Bailey

Jenna & Bailey

September 21, 2024 • Watertown, SD

How It Started

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Bailey- "Jenna and I met last June at a Jake Owen concert in the Harrah’s parking lot where the guys started tailgating and the girls were on a walk with her dog Trigger. We were introduced by my best friend Mitch. After some liquid courage, I walked up to Jenna to give her some grief about her beer of choice, and she dished it right back at me. We were inseparable the rest of the night and talked about everything under the moon. I asked Jenna to go to mass with me the following morning and breakfast afterwards. The next morning Mitch and I went to pick Jenna up at her apartment and we went to mass together and breakfast. Jenna has always been intentional from the get-go, so our first date I was getting all of the hard questions. I must’ve answered all of the tough questions okay. ;) Looking back on this weekend I am extremely blessed to have met the girl of my dreams when neither of us were looking. Everything happens for a reason and that weekend is the definition of that as I bought a concert ticket earlier that week and Jenna decided to go to the Jake Owen concert the previous day."


Jenna- "I first laid eyes on Bailey on a warm June summer day at an outdoor country concert tailgate. I was preoccupied playing with my puppy Trigger and hanging out with my best friend Lindsey and other various girlfriends. I did notice a new face in the mix of my male dental school classmates. He was introduced to me as my classmate Mitch's best friend and financial advisor from South Dakota. I thought right away that he was quiet and very polite. I was slightly confused why a financial advisor was wearing cowboy boots, but that thought quickly passed me by as I began to enjoy the night with my friends. A few drinks and hours later, Bailey approached me and began teasing me for the brand of beer that I was drinking. I quickly held my own which turned into playful banter, and we were inseparable for the rest of the night. We quickly merged our friend groups and our into the night conversation consisted of our hobbies, our families, and our faith. Bailey asked me to go to mass the next morning before leaving that night. After mass and brunch the next day, Bailey left on the four-hour drive to return to Watertown for the work week and just like that, the best summer of our lives began."

A trip to Watertown

Picture of A trip to Watertown

Bailey- "A couple weeks later Jenna had a rotation in Grand Forks, so she decided to come to Watertown for a weekend. I showed her the best things Watertown has to offer. She knew Watertown and I were a package deal so I did whatever I could to spruce it up. We spent a lot of time with friends on the lake that weekend. We had great conversation, and I knew I really liked this girl, although she was leaving for a dental mission trip for the month of July!"


Jenna- "I was able to come visit Watertown for a quick weekend in order to spend some quality time with Bailey. I was leaving to go to the Dominican Republic for the next 4 weeks, so I decided that I wanted to be intentional about this from the beginning. This was the first time that I got to see Bailey be a dedicated and loving son, brother, and friend. I knew after this weekend that I wanted to stay in close contact with him amidst the next few crazy months to come."

Officially Dating

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Bailey- "I was going to We-Fest with my best friends the first weekend she was getting back from her mission trip, and she made a last-minute decision to get a ticket. This is where we became best friends and our relationship progressed. There weren’t many weekends after that weekend that we didn’t spend together."


Jenna- "In August not only did I see Bailey the financial advisor in cowboy boots, but he also added a cowboy hat. That's all it took, I was hooked! In all seriousness, the next few months showed me Bailey's best qualities of patience and commitment as we began a four-hour long-distance relationship with me spending hundreds of hours studying for my dental board exams and Bailey staying busy with work. Bailey said it best- we did become best friends and that was the foundation of it all. Whether we were playing a competitive game of HORSE on the basketball court, going for walks with Trigger, or playing various card games, we quickly learned that every part of life was better spent together. The following fall months brought sweet memories of meeting and spending time with each other's families that I will cherish forever."

Cordell Family

Brad, Amy, Jayden, Anna, Summer, Grady, Cole, Jenna, Bailey

VanSickle Family

Bailey, Troy, Taylor, Sandy, Nick

Ehlis Family

Jenna, Bailey, Jada, Brock, Tara, Elliott, Joshua, Paige, Gage

Taking the Next Step

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Bailey and Jenna began prayerfully considering the sacrament of marriage and starting a life together.

In February of 2024 Jenna signed an employment contract to work for a dental office in Watertown where she will begin working after graduation in June of 2024.

The Proposal

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On March 3rd, 2024, during the week of Jenna's last spring break Bailey surprised her by dropping to a knee on the beach to ask the big question. The easiest yes!

Celebrating with Best Friends

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The engagement was followed by a week of pure bliss down in Cancun with the couple's best friends.

The Beginning of Forever

Picture of The Beginning of Forever

Bailey and Jenna purchased a home in Watertown where Jenna will live the summer after graduating dental school and where the couple (and Trigger) will live together after their wedding date in September. We cannot wait to host family and friends and spend quality time out on the lake in the backyard!

Thank You

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Thank you to all of our beloved family members and selfless friends that have stood by us, offered countless prayers, and supported us through our walks of life! We can't wait to celebrate with you all!