Engaged (Part I)

Because one proposal isn't enough.

Life Update: Lucy and I are engaged!

My mind is galloping, skipping, spinning like a record player from a yard sale. Engaged. We are ENGAGED. I have dreamt up this moment for so many hours of my life. I remember my teenage self sitting at the desk in my childhood bedroom, marveling at my MacBook as a YouTube video showed a man proposing to his future hubby at Home Depot while Betty Who’s “Somebody Loves You” echoed through the warehouse walls. I remember playing and replaying the flash mob in Disney World as I imagined my future Cinderella cheesing. I love witnessing love—seeking it out in every moment like a page out of Where’s Waldo. I’ve seen it all—when “Big” proposed to Sarah Jessica Parker with a stiletto in Sex and the City, when long-serving bridesmaid Katherine Heigl was proposed to at a wedding in 27 Dresses, when Jimmy Fallon got down on one knee and asked Drew Barrymore to the Red Sox home opener in Fever Pitch. And now the time has come for me to flex my rom-com muscles and do the dang thing.

It went down on a Saturday afternoon.

⏸️. Before you read any further, I will answer the burning FAQ: Did Lucy know it was happening? Yes. 100% yes. We had picked out our rings two months prior, and for the last week leading up to the big day, I brought up our future engagement in every conversation, like a little kid getting hyped for their birthday. “So when do you think we’re getting engaged?” I’d ask on every walk and over every meal. Lucy would give me the look—the one where her blue eyes pierce into mine and read my every thought.

▶️. Lucy and I had just biked the 50-mile roundtrip trek from Chicago to my hometown Highland Park. A ride we’d done about ten times now, but never against gusts over 20 mph until that Saturday. We pedaled through the wind tunnel for four hours—something easy-breezy for Lucy felt like an Iron Man on my quads, which hadn’t seen a squat rack since college. But with five minutes left, the adrenaline kicked in as I mentally prepared for the most important single-legged squat of my life. This was it. On the last mile, I scoped out a vacant area along the concrete crust of Lake Michigan. Bingo.

“Can we pull over?” I turned my handlebars to the left, and Lucy played along with my charades, knowing better than to ask why. We laid our bikes down, and I avoided eye contact as I proceeded to ask the question that would resolve any brain cell of Lucy’s that still contemplated whether it was happening:

“Can we dance to a song?”

In the weeks leading up to our engagement, I had conditioned Lucy with spontaneous solicitations to dance. In our hotel room in Cali and in our kitchen in Chicago, I invited her to sway with me to Sam Smith and John Denver. Despite the conditioning, my request to dance in front of Lake Michigan was anything but subtle. Lucy did her giddy giggle—a light laughter that rolls off her tongue when she’s overwhelmed with joy.

I pulled out our portable speaker and played a song written and sung by yours truly (shoutout to my coach Ben—for putting together the most magical instrumental and for believing in me as if I had the vocals of Shania Twain). Five months into dating, Lucy and I attended a OneRepublic concert. The band’s lead singer, Ryan Tedder, is also the songwriter behind masterpieces for Beyoncé (“Halo”), Leona Lewis (“Bleeding Love”) and Adele (“Rumour Has It”). That night at the concert, Lucy turned to me.

“You’re going to be a songwriter one day.”

No bluff. She meant it. I laughed in my head. Me a lyrical genius?! I decided that if I were to ever write a song one day, it’d be for her—the first and only person on this planet to call me a songwriter.

Lucy and I swayed side-to-side—just as we had practiced in our kitchen—as my first single “Future Forever” blared from the speaker. I sang my way through our origin story, starting with the first time I spotted her on the basketball court at rec league. As the song neared the end, I went into my backpack and retrieved the velvet box along with a giant sherpa blanket. Typically, I’d bring a smaller backpack on our rides that contained Gatorades, Advil, bandaids, protein bars, a Diet Coke for Lucy, dry shirts, sometimes sweatshirts too, and a deck of playing cards. But the 30+ square-feet of sherpa fluff required something a bit heftier. Imagine a Personal Item that barely squeezes into an airline’s metal frame sizer at the gate.

Before we headed out on our bike ride that morning, Lucy and I had this exchange:

Me: “I packed extra sweatshirts in case we get cold.”

Lucy: “Is that all you got in there?”

I could sense Lucy’s smirk as she walked her bike in front of me before saddling up. That is the moment I knew she knew.

But there’s no way she knew the extent of this moment. My tone-deaf vocals serenading her with lovey-dovey lyrics that could nauseate an audience of non-romantics, as a big fluffy banner displayed a selfie of us and the written words Lucy, will you marry me?

I got down on one knee and imagined all the straight men who came before me. I rambled, said how three years ago we pulled over on our bikes just as we did now. We hadn’t started dating yet, but we sat in the grass and watched Navy Pier fireworks as two super platonic friends do. 1043 days later, we stood next to Lake Michigan, its water our only witness to my proposal preamble that would eventually lead to:

“If it’s okay with you, I’d like to marry you.”

Never in a rom-com script had I heard such an unromantic, pragmatic line. But it worked—LUCY SAID YES!

***

As I write this on May 25, 2025, it has been approximately fifteen days since Lucy acquired her bling. It has been fifteen days of me prying Lucy: “WHERE’S MY RING?!” Now sixteen days. In Lucy’s defense, I had said I wanted to propose first, and she granted me exclusivity to do so until Labor Day weekend; then all bets were off. But COME ON. The ring is somewhere in our apartment, and it’s taking every bit of willpower not to peruse the premises like a page out of Where’s Waldo.

So that brings us to halftime folks! Stay tuned for Part II of The Proposals…until then, a few initial reflections and wonderings:

• To my friends who are married: How many arguments does it take to plan a wedding?

• To my friends who are unhappily single: Join a rec league.

• To Uncle Bob: Thank you for finding and creating our dream rings. Can’t wait to see mine in real life…

• And to my fiancée: I can’t promise you I’ll ever have the vocals of Shania Twain, but I’ll never stop serenading you and dancing through this life with you.