How Lovely and Giddy Is This Marriage Proposal? – Cup of Jo

On this dreary January day, let’s talk about something sweet: a marriage proposal! Chris and Kyle recently got engaged, and here’s how it went down…

First, tell us about the secret planning.
Kyle: Chris and I had talked about marriage for a while, but I had a moment a couple weeks ago when I was like, all right, I’m going to do this, and I’m not the kind of person who can sit on information for too long or I’ll get anxious. So, I called my mom — I’m from 90 minutes outside New York City — and she took me to a ring shop in our Pennsylvania hometown. It was a very unassuming corner store. When I walked in, I saw exactly what Chris wanted: a simple, round silver band.

Did you have a vision for popping the question?
Kyle: I workshopped a few proposal ideas with Chris’s best friend and my best friend. The #1 most meaningful thing for him is being with our people. Since we were planning to go to his hometown, Rochester, for the holidays, that seemed like good timing.

Oooh, that’s exciting.
Kyle: The week leading up, I was probably the most stressed I’d ever been. I went through every possible thought, positive or negative. I called Chris’s parents, too, to tell them I was planning to propose. His dad is the nicest guy, and he said, ‘Oh my, I’m smiling ear to ear.’

What happened once you got to Rochester?
Chris: After hanging out with my family for a few days, Kyle and I went to a local Christmas market with his best friend, my best friend, and both of their partners.

Kyle, what was your emotional temperature at this point?
Kyle: On the way to the market, Chris is driving, I’m in the front seat, and our friends Molly and Mel are in the backseat. My heart is pounding, and my hands are shaking. Mel texts me, ‘You good?’ I’m like, ‘No.’

Chris, did you suspect anything?
Chris: We were walking around the market, and I’m not thinking anything of it. We see this photo opp place, with a cute snowman bench, and we decide to take a group picture. Then, randomly, I’m like, Kyle, why don’t we take a picture with just us?

What perfect timing.
Chris: We’re sitting on the snowman bench, and Kyle says, isn’t it cool that both of our best friends, our favorite people, are here together? And I was like, yeah, smile for the camera! And he was like, well, I planned this. And I was like, yeah, I know, I was on the text thread. And he was like, no, I PLANNED this. And I’m like, okay, I mean…thank you? And I’m looking at the line that’s forming, and I’m like, we’ve gotta snap this picture and go. But then he started going into his spiel. And after that I don’t remember what else he said.
Kyle: I completely blacked out, too!

So, no one knows or will ever know what was said.
Chris: Yes! Now I’m in shock, and I’m side-eying my best friend so hard, like, This is happening! You knew about this! Kyle gets down on one knee. And I said, ‘I WAS NOT EXPECTING THIS!’ and enthusiastically said yes! When I get surprised, it’s not that outward experience, like gasping and jumping; instead, it almost feels like I’m playing a video game of my life. All I could ask him is like, who knew? Did the snowmen on the bench know? Who knew about this, Kyle?! Then I put the ring on, and we exchanged stories.

Did you celebrate afterward?
Chris: We went back to my family’s house for a Champagne toast, which was so, so nice.
Kyle: Chris has a huge family —  he’s the oldest of 23 cousins, and they all act like siblings — so you can’t just tell everyone to park around the corner because there are like 40 cars! So, as we were driving up, we saw cars everywhere, and Chris immediately knew.

What do you love about each other?
Kyle: We met just as I was coming out, and we talked about it, and he was like, ‘Your opening up to me just makes me want to be close to you and support you.’ That fit very deeply into my heart from the beginning. Plus, honestly, just how much fun we have. We can turn that dial to 100, or back to zero if we need to take a beat. Ever since our first date, it was very clear that that spark got lit inside me.
Chris: I love Kyle for so many reasons, and one of them is his welcomingness — he always says, ‘I want to merge my people.’ Now our friends have become friends, and everyone looks forward to seeing each other. In a world where people often keep things online, he is very ‘let’s all come together.’ Everyone everyone everyone wants to be friends with Kyle, which is going to make our guest list so very hard.
Kyle: I also have an anxious dog, Ginny — she’ll keep her distance before she lets you pet her. But now she always wants to sit on Chris’s lap and sleep next to him. She’s like my child, so their connection means so much to me. Right before we left for the Christmas market, I said to my dog, ‘All right, today’s the day, I’m going to propose to Chris,’ and, without my asking for it, she gave me a high five.

Congratulations, Chris and Kyle!

P.S. More great proposal stories, and the best part of weddings.