The Ultimate Promposal The Ultimate Promposal
Catesby and Jacob took a trip to New York City from Virginia to see The Prom on Broadway. Catesby had been planning his surprise proposal... The Ultimate Promposal

Catesby and Jacob took a trip to New York City from Virginia to see The Prom on Broadway. Catesby had been planning his surprise proposal for a few weeks. He handmade a box for the rings that was thin enough to keep in his pocket inconspicuously. On their five-year anniversary, Catesby surprised Jacob outside of the theatre to pop the question. The two wore tuxes to fit the prom theme of the musical, something Catesby had come up with as a ‘fun date night idea’. After an early dinner reservation, the two took a stroll to the theatre where they picked up their tickets. With two sneaky photographers in a pre-scouted location, Catesby faked out Jacob by pulling out two boutonnieres. After fastening the boutonnieres, Catesby pulled out the rings as the final surprise.

Q1: Let’s start at the beginning. How did you two first meet?
A1: I was a recent college grad living in the “Fan” neighborhood (a fun area with a great bar scene) in Richmond, VA, in a house with a very active social schedule. However, through all that fun, I never seemed to meet a guy that I had much of a spark with. I had chatted online with Jacob off and on over a couple of months, and on June 21, 2014, decided to meet him for a cup of coffee. I don’t know if it was love at first sight, but I will never forget the joy in his smile, and the excitement in his wave as we approached each other outside of the Lamplighter coffee shop halfway between our apartments. We greeted each other, ordered our drinks, and went for a walk around the city. We ended up walking, exploring, and talking for hours, and by the end we both knew that this was the start of something special.

Q2: What makes your relationship special? Tell us some things that you both value in your time together. (example: pushing each other to new limits, love to travel, huge comic book fans, foodies, etc.) What makes your relationship unique?
A2: What we love about our relationship is our ability to communicate with each other about anything. We love going on long walks exploring our own city or places abroad, we’re both curious about how things got to be the way they are, we have a lot of the same interests without being altogether too similar, and we do bring out the best parts of each other and push each other to be better. We can quote Family Guy, American Dad, and the Golden Girls with utmost precision. The default playlist in our house is Sirius XM72 On Broadway.
Over the past three years, we completed a major renovation of a ninety year-old house in the city, doing all of the work ourselves. It took a lot of cooperation made us be very honest about what we expected of each other,  and we our relationship is much stronger because of it. During that same time frame, Jacob was working hard to maintain and build a high school choral program, and I got to enjoy being a “show choir dad”, building sets, driving a trailer and running stage crew for the students. It’s neat to think that our relationship is just a normal part of life for his students.

Q3: How did you know your partner was the one? When did you first know this in your relationship? (these may often be the same moment, but aren’t always)
A3: Over five years of knowing someone, it’s hard to pinpoint the exact moment you know you want to be with them forever, but it became clearer all the time. I couldn’t imagine having anyone else by my side while renovating a house. Whether it was tearing down a wall or sitting in the crawlspace with a blowtorch and a fire extinguisher for soldering plumbing, there was always something to discuss or a funny observation to be made. Learning about each other’s pasts made it obvious that we have very similar souls, and maybe that means we’re meant to find each other.

Q4: Give us all the details about the proposal. How and where did it happen? Was it a surprise? What was the planning process?
A4: For years, we had joked that it was Jacob’s responsibility to propose to me. He was going to have to ask my parents and the whole-nine-yards. Even our friends and neighbors knew. He is a high school choir director, so he wanted to plan something fun with his students to surprise me.
We were watching the 2019 Tony Awards and learned about the musical “The Prom” about a gay teenager and the Broadway actors who swoop into her small town and try to force the community to allow her girlfriend to be her date to the prom. We loved the number they performed on TV and would later fall in love with the soundtrack. We looked at our schedule for the summer, and realized if we were going to go it had to be soon. We book our tickets for June 21. Jacob was excited about the trip, but overwhelmed with end-of-the-year activities at school and so I took care of most of the planning. When it hit me that we were going to be going to see such a relevant show on the five year anniversary of us meeting, I started to realize that this might be the perfect opportunity to propose. I began messaging with friends in New York or who had a connection with Broadway, messaging the show and the theater itself on Facebook, and trying to figure out how I could make this happen in about 10 days.

Q5: We’re all about the bling… Tell us all about that ring!
A5: We knew that we wanted to go with something simple, standard, and classic. Gold bands were the clear way to go. We realize that we’re among the first generation of couples to have a relationship and know almost from the start that marriage and a publicly acknowledged engagement would be a possibility, and having these simple gold rings reminds us that our marriage will be just as normal as everybody else’s.

Q6: Are you excited to start planning your wedding day? Do you have any ideas in mind yet?
A6: We are so excited to plan our wedding day. It’s an amazing feeling just knowing that it is going to happen! We have a few ideas for venues around Richmond that we would love. There are a lot of places that are special to us, but we are still so early in the planning process that it’s hard to know what we will end up doing.


Location: Times Square
Second Shooter: Kenneth Gronquist
Photographer: Megan Breukelman Photography