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How I got engaged — and why

I can't stop looking at my hand
We went ring shopping twice. He bought what he would have bought had we not gone shopping. And it's perfect.
In early August, I believe, Drew took me on a dinner date to Chinatown, where I had chicken curry in a coconut and he made fun of me for using chopsticks. (He’s just jealous of my hand-eye coordination.) We strolled around outside for a bit, enjoying the summer evening, eventually ending up on the 18th Street bridge overlooking the canal and the Downtown Chicago skyline. We stood there for what must have been a couple hours, watching the trains, bouncing from serious to silly conversation, mostly about past relationships and how incredible the last few weeks had been.

“Do you feel like you’re in a place where you’re ready to be in a relationship?” he asked me. One of the things I love about him is that he wants to avoid assumptions, favoring clear communication instead. I considered a few moments before giving him the obvious answer.

Some people remember their first kiss with great fondness. For me, the first time he hugged me, that night on the bridge, will always be “the beginning.” It was an incredible feeling that I had finally arrived at a place I had been searching for. He wouldn’t kiss me until weeks later, but the joy in that hug must have shined through: Both of us cracked up moments later when a passing car honked in celebration at us.


Last Friday was the end of a rough week. (Project launch weeks usually are.) I was sleep-deprived, hormonal and mentally fried, but feeling better after dinner (Drew had suggested Chinatown, but I wanted tacos) and frozen yogurt (Drew told me about the bond market and I teased him for wanting to eat ice cream in the dead of winter). I expected to feel even better after he dropped me off at my apartment, because I intended to fall asleep immediately.

Instead, when we climbed in his car, he said, “Do you feel like going for a ride?”

In the seven months I’ve been dating Drew, he has never suggested we go for an aimless drive.

He’s going to do it. He’s going to ask. He’s going to do it TONIGHT. No, no, no he’s not. Just calm down. You’ll be disappointed if you’re wrong. Everything’s fine. Maybe he really does just want to go for a drive.

“Why the heck not? Beats sitting in front of my building and freezing like we usually do,” I laughed, my heart pounding a mile a minute.

He headed south on Lake Shore Drive, past Soldier Field, then west. He was heading to Chinatown.

He pulled over on the 18th Street bridge and asked me if I remembered standing here back in the summer.

“That was a great night,” I said. We’re sitting in the car. He can’t propose to me while we’re sitting in the car! That would just be weird! “Do you mind if we get out? The view is so pretty, but I can’t really see it from here.”

The snow on the ground was at its iciest. We stood there on the bridge, both shivering uncontrollably, both pretending nothing abnormal was going on at all. As if the weather were not inconvenient enough, I am afraid that I made setting any kind of mood very difficult for him, as I had defaulted to my natural nervous tic of cracking jokes left and right (I am so smooth).

Finally, in a pause, he said, “I still remember some of the conversations we had that night verbatim. This is where I asked you to be my girlfriend, and I since I had pretty good luck with that, I figured, what better place to ask you to be my wife?”

I don’t know what sort of look I had on my face, but it prompted him to add, “Seriously!” as he pulled a box out of his pocket and opened it.

Silence. I stared at the ring, stunned. I want to say yes! But there’s nothing for me to say yes to! He hasn’t actually asked me anything! This realization was enough to break my frazzled brain. I looked back up at him, and down at the ring, and up at him, and down at the ring, and up at him. Finally, I blurted out, “You haven’t asked me a question yet!”

I clearly have no idea where the camera actually is.
I clearly have no idea where the camera actually is.
With a rather panicked look on his face, he said, “Heather Billings, will you be my wife?”

The passing cars honked a chorus as he put the ring on my finger. Whether he was shaking from the cold or nerves, I couldn’t tell. I was shaking too.

We went for coffee afterward, because sleep was obviously not going to happen at that point. I teased him about not doing the one-knee bow.

“I meant to get down on one knee!” he said. “I didn’t get down on one knee?!”

We stayed until the 2 a.m. last call, talking about how relieved he was not to be carrying the ring around in his pocket any more, how the 3D Javascript rendering on diamond purchasing websites crashes most browsers, how strange it felt to use the word “fiance,” how natural it felt to be engaged.

“I figured it was about time I put my money where my mouth is,” he said.


I knew from the very beginning that there is something different about Drew. Talking with him is effortless. Silence is comfortable. He keeps up with my crazy lateral jumps in conversation — and is prone to the same sort of thinking himself. He is intellectually present in every moment, even when we were joking about the pope pooping in the woods. He seeks to learn from his mistakes and he embraces the fact that he needs God’s grace in his life. He can be goofy, serious, or brutally honest, but underneath it all, you know that he wants more than anything to do the Right Thing for the Right Reason. It was always obvious that he has a gigantic heart to match his towering stature. And somehow, somehow I don’t quite understand, he makes me a better person. I use that language with hesitation, because he doesn’t fill a hole in my life or make up for my character flaws. He’s not my “other half” or my “soulmate,” two ideas I have always found ridiculous. But when I look at how he runs his race, it makes me examine and adjust how I run my own. There’s a feeling of connection, based on honesty and openness, I didn’t know could exist. I am humbled by his selflessness and encouraged by his generosity. Does he have flaws? Of course. Am I going to hate his guts? At times. But there’s something about the idea of life with this guy that is reassuring where other relationships have been frightening. I don’t expect to be “in love” for very long at all, but if these things are even a small indication of the man God’s making him into, I am a blessed woman indeed.

Now if only I could get someone to plan the wedding for me.

Published in Family My Life in Boystown


  1. Anastasias


    The sweetest thing!!! OMG! I am so happy for you both, can’t wait to hug you two when I see you next!! OMG, what a treat!!!!!!

  2. Linnea


    Beautifully written story of what will no doubt be a beautiful life together!!!! Best wishes, Heather!!!

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