Kaitlin and Ben


Kaitlin's Proposal in Orange, VA

How We Met

Ben and I first met in fourth grade when I moved to Central Virginia all the way from Tennessee. In 5th grade, I would constantly tell him for cutting paper in his desk and trying to talk to me while our teacher was in front of the class. When Ben and I got to middle school we started dating in seventh grade. In true 2009 fashion, he asked me to be his girlfriend through Facebook messenger! Middle school is already awkward, but it gets better. Ben and I’s first date was with my parents. They took us to Chili’s and sat at the table behind us. Ben was so nervous that he spilled his entire drink on himself and I’ll never let him live that down. After dinner, we went bowling with parents still in tow. When we were leaving, Ben tried to hold my hand and I quickly shut it down before my parents realized what he was doing. In the months following, I wouldn’t let Ben sit with me at lunch and get this: neither of us had cellphones. So, every day we had to figure out when we could log onto our family computer later that evening and message on Facebook.

Ben and I were clueless about how to be a boyfriend and girlfriend. After all, I was 13 and he was 12. Once Ben and I got to high school, dating was like a fairy tale. We were the cheerleader/football player couple and our Senior year we won Prom King and Queen. After high school, we knew we were not going to attend the same college. I was originally from Tennessee and was moving back to attend the University of Tennessee. Ben signed to play football at Shepherd University in West Virginia. For the first year, we were over six hours apart. I would drive to West Virginia to see him almost every other weekend. After our Freshmen year, he transferred to Radford University of play rugby. There were still about three hours of distance between us, but it was way better than six. Ben finally graduated from college in December 2018. Long-distance was so hard, but we finally ditched it and we moved in together in 2019.

Engagement Proposal Ideas in Orange, VA

How They Asked

I had my suspicions for a couple of months that Ben might propose, but I tried my best to stay calm and just let things happen. On Saturday, my best friend Caroline picked me up from my house super early and we headed to her house for a “girls day,” or so I thought. I had a cute outfit planned because at first, I thought we were going out to celebrate my birthday last month. Ben and Caroline planned a fake photoshoot instead to throw me off his trail. Caroline and I were supposed to meet Ben at a cute park in the middle of town. On the drive into town, I started getting emotional thinking that it might actually happen. Caroline started to drive the “wrong way” and the next thing I knew we were pulling into the parking lot of our high school football stadium. Ben’s best friend, Dominique was waiting for us outside the gate. Instantly, I knew that it was happening. As Caroline and I were pulling in the parking spot, she hits a huge pothole and we both going flying out of our seats. When I finally got myself together, all three of us were laughing so hard at our grand entrance. As I walked into the stadium, I had Caroline to my left and Dominique to my right. I look down the field and Ben is standing at the fifty-yard line. The walk to him felt like an eternity, but as I got close enough to talk to him I was immediately overcome with emotion. I looked at Ben, with my hand on my chest and said, “Benjamin.” I couldn’t believe that I was in the middle of something I had dreamt about since we starting dating in middle school. Ben bought me a beautiful bouquet of orange and yellow flowers. He then looks around the stadium and says, “It’s been a while since we’ve been here huh?” I think the nerves were at an all-time high for both of us and I was so ready for what was coming. The next thing I knew, Ben says “You have been my cheerleader since 7th grade and I want you to be my cheerleader for the rest of our lives, Kaitlin Taylor Phifer, will you marry me?” I paused for a couple of seconds because I really wanted to be in the moment with him. Of course, I said “YES!” He slipped the ring on my finger and finally, it was mine! In months prior, I had shown Ben rings that I liked, but he did so good picking out the one that I had been looking at pictures of for over a year. Ben had a close family friend take pictures of the proposal and she was amazing. He put so much effort and detail into the proposal. Pictures are very special to me and Ben knew that we would treasure these.


Special Thanks

Emily May
 | Photographer