Caitlin and Brent

Engagement Proposal Ideas in Indianapolis, IN

How We Met

In 2006, we met very briefly, in the cafeteria of our high school when Brent was selling tickets for some event. He was a senior and I was a sophomore. I remember wondering who “the swimmer with those eyes” was (his are such a dark shade of brown, they appear black, in a lot of lightings), but he remembers nothing from that moment.

In 2008, we really met when I began dating Brent’s roommate. I remembered that chance encounter in our high school cafeteria and finally knew who he was. We both remember loving our first conversation and being sure that we could end up being really good friends with one another. We, especially, appreciated each other’s knowledge and taste in movies. When Brent’s roommate and I broke up, Brent and I stayed friends. Over the years, we hung out every few months or so, double dated with our significant others, talked on the phone about life, and helped each other with classwork (really Brent helped me), and celebrated happy events in each other’s lives, including Brent’s first wedding, where I happened to catch the bouquet.

In 2016, Brent’s first marriage ended in divorce, just as I was getting engaged to my boyfriend of 2.5 years. Then, in early 2017, my engagement was abruptly called off the day before I was set to send the save the dates out. On Easter of 2017, we went for a walk around my neighborhood, catching up on everything that had happened in our lives, when we realized that in the 9 years of knowing each other, we had never spent time together, alone, and there was clearly something more than friendship sparking between us. 4 weeks later, we went on our first date and the rest is history.

Where to Propose in Indianapolis, IN

How He Asked

We live in Irvington, a former small town that is now a historic neighborhood in Indianapolis, known for its Halloween festival. At the festival’s Masquerade Ball, in 2017, we saw a man live painting the event. I made a comment that if we ever got married, it would be amazing to have someone live paint the reception.

There’s a park, about a block from our home, that we love to walk to, run around, and sit at the fountain in its center. There are many little details that we love: the fountain, a bust of Washington Irving (the author our neighborhood is named after), a dish for our dogs to drink out of, and all of the beautiful, old homes that line the sidewalks surrounding the park.

On the night of July 19th, we went to dinner at my favorite neighborhood restaurant. Then, as we often do, we got ice cream at the neighborhood ice cream parlor and took a walk around our neighborhood. I happened to suggest walking around the circle. As we approached, we saw a man painting a large canvas, in the park and I suggested that we go up to see if we could look at what he was working on. As we approached, the man stepped away, revealing a painting of two people, dressed exactly as we were dressed, getting engaged next to a man painting the painting we saw before us.

Brent said, “This is Nicholai Shaver. He painted the Irvington Masquerade Ball… I got him to agree to paint this piece tonight…And he’s agreed to paint our wedding reception.” Brent got down on one knee and asked me to be his wife. Obviously, I said yes.

Special Thanks

Nicholai Shaver
Artist
Bailey Wheeler
Photographer