Jstyle Weddings spotlight | Sydney Davis & Aaron Levitan

How did you meet?

We were set up by a mutual connection. I (Sydney) was getting coffee with a friend’s coworker to talk about the ad tech industry and she asked if I wanted to be set up. She and Aaron were acquaintances and she had just met me that day, so it’s pretty lucky she made such a good match.

Do you have any interesting stories to share about getting to know one another?

We have a pretty classic COVID love story. Our first date was March 7, 2020 and COVID didn’t even come up on our first date. The next week, I (Sydney) went to Cleveland for what I thought was the weekend and ended up staying for almost six weeks. Aaron and I started texting every day, then talking on the phone, then FaceTiming until it was obvious that this was something special and I knew I had to go back to Chicago. Shout out to my brother Taylor and my dad Jeff for driving me there in the heat of the pandemic!

How long did you know each other before you got married?

About 2¹⁄2 years.

When did you know you wanted to marry your partner?

Sydney: The July after we met, about four months in, we drove about 14 hours to Denver (there was still a bit of a stigma around flying) to visit Aaron’s sister for a week. It was our first trip and our first time spending a long period of time together, and it was an adventure. We went on several hikes, rode bikes and explored the city. One day we went on a long bike ride on a trail and got caught in the rain. We found shelter and were waiting out the rain together, wrapped up in all the layers we had. In that moment, I not only knew I loved Aaron, but that he was my person and that we were going to end up together.

Aaron: It was during our trip to Denver in July 2020. In that one week, we experienced many ups, downs, challenges and triumphs – very much like a marriage! Since it was one of the best weeks of my life, I was pretty sure I wanted to marry Sydney after that.

What was the best part of wedding planning?

The cake and food tastings, of course.

Was there any spot-on advice you received prior to the wedding?

All the recommendations everyone gave us for vendors were amazing. We were thrilled with all our choices and could not have asked for a better team.

Separately, I (Sydney) was also glad that I bought a second look dress, just in case. It was so freeing to be able to change into a mini dress!

Were there any conflicts between the two of you or your families in the planning process? Did either of you have to make any sacrifices?

Not really! I’d say we were super aligned. The only tough part was narrowing down our list, which I think is a struggle for everyone.

What was the most fun or interesting Jewish aspect of your wedding/partnership?

We loved the energy of our ceremony. Rabbi (Joshua) Skoff and Gadi (Galili) did an amazing job in leading with Jewish traditions while tying in modern, joyful elements to make it feel personal to us.

We also had an extremely high-energy hora! Aaron’s dad even fell off the chair. Don’t worry, he was OK and attributed his toughness to the fact he regularly does yoga.

“Immediately after the ceremony, we had 20 or so minutes to ourselves where we could read our vows to each other privately. It was an intimate and special moment we will never forget. Then, of course, everyone hit the dance floor immediately after the cocktail hour and the energy was unbeatable!”
-Sydney and Aaron