When we ask newlyweds to think back on what they wanted most for their big day — and we’ve interviewed hundreds of them over the years — the most common response is “For it not to feel like a wedding!” But in a monsoon of flower crowns and macaron towers, how do you see beyond the usual tropes and actually pull off a non-cookie-cutter affair? For the answer, we decided to interrogate the cool couples whose weddings we would actually want to steal — right down to the tiger-shaped cake-toppers.
Here, we spoke with two vice-presidents at two start-ups: Maddie Garber, who works at smartlock company Latch, and Chris Burwell, who handles operations for the hotels app One Night. They were married Halloween weekend in 2017 under the soaring ceilings of the Weylin, which used to be the Williamsburgh Savings Bank. A family friend officiated, and another family friend — Bobbi Brown — did the makeup. The couple took tequila shots under a chuppah, served guests a steakhouse dinner, and ended the night in the vault.
Maddie: When we got engaged, my parents were like, “Oh, well you’re going to have Steve” — my childhood rabbi — “marry you, right?” Chris is not Jewish, and we’re both not religious at all. But we are so close with my family; they live right there in New Jersey.
Chris: And my mom really wanted to bring a piece of Oregon and the West Coast to the wedding, since we were having it in New York.
Maddie: When we met, I didn’t really know anyone who grew up where he grew up, in southern Oregon.
Chris: I went to law school with one of her friends from Tufts. I kept hearing about her over the years and I saw her picture and told the mutual friend, Sophia, that she should set us up on a date. Finally, in my last year of law school, she did.
Maddie: He was someone who lived out of a van and went climbing every weekend and kayaking, all these crazy things. After college in Colorado, he went to Paris, then lived in California, then was living in New York as a lawyer. It was a much more adventurous path than I’d had. I grew up in a liberal Jewish bubble in Montclair, New Jersey. It turned out the two different perspectives were a nice match.
Chris: The night I proposed in our kitchen in Cobble Hill, I had coordinated it so that her parents and brother were waiting at the restaurant where we were going after.
Maddie: We were getting ready to go to dinner at Four Horsemen, our special restaurant. He just started talking and I didn’t realize he was proposing. We’d been together less than two years.
Chris: It was a pretty easy decision to get married at the Weylin, once we saw it. It’s an old New York City landmark, but in some ways it has this very European, old-world vibe.
Maddie: It has all the original wallpaper, the original elevator, they peeled all the vinyl off the stairs. It’s just an amazing space.
Chris: It’s obviously a well-run operation, too, and we could really see how the party would play out, with the 200 friends and family we wanted to have there.
Maddie: We found a way to do something really cool that would honor the fact that I am Jewish, and just look amazing — the chuppah, in this laser-cut metallic fabric. The gold looked really cool in the space.
Chris: We ultimately decided not to have a religious figure officiate but instead a family friend, a dear friend of Maddie’s family who I got to know when we started dating.
Maddie: Her name is Harriet but I’ve called her Howie my whole life. She is a spiritual person, even though she’s not religious, and I knew that she would bring a certain level of gravity to the ceremony. It also meant a lot to my parents, who were probably a little disappointed that it wasn’t going to be a rabbi.
Chris: We broke the glass, and it’s a tradition in a Jewish wedding that you drink wine, I think, but instead of drinking wine we all took a tequila shot at the end of the ceremony. It was our spin because Maddie and I love tequila.
Maddie: And it was also a longtime family friend who did my makeup. Bobbi Brown is from Montclair, and she and her husband have been very good friends with my parents for like 25 years.
Chris: Honestly, I was way more starstruck by the DJ we booked, Kenan, who’s half of the duo Chances With Wolves. I used to listen to them in graduate school and couldn’t believe that it turned out Kenan did weddings.
Maddie: When Bobbi offered to be my makeup artist, we did a little test run, but I didn’t tell her what I wanted. I feel like you don’t really tell Bobbi Brown what to do. I did tell her I didn’t want a loud lip color. She does an amazing job of making your skin look really great. I’ve been at so many weddings where they do the airbrush foundation, and it’s just weird. She just made my skin look really good and dewy. I had a bronzy color on my eyelids, she filled in my brows, and I did have fake lashes on, but that was really it. It was just very natural. I didn’t have a bridal party, but Bobbi also did my mom’s makeup and my grandma’s makeup — and she had two people with her who did the makeup for Chris’s mom, my aunt and cousins, and a few of my friends.
Chris: I got ready in my parents’ room, and the whole thing felt very surreal, to have them in New York with me putting on a tuxedo and us looking at each other like, “Oh, I’m actually getting married.” The Wythe has this incredible view and roof deck and so Maddie was waiting there for our first look. It’s kind of clichéd, that your breath is taken away or whatever, but her on the roof, with the city behind her … We actually have a big blown-up picture in our apartment of the moment I first walked up to see her.
Maddie: I wore a dress by Elizabeth Fillmore that I found during a trunk show at Gabriella Bridal in Soho. I’m a decisive person. I had no interest in trying on 50 dresses. I picked up this long dress and tried it on and Elizabeth came over, like “Do you like it?” I said, “I do, but I don’t really think I want to wear a long dress.” And she just started pinning it and shortening it and all of a sudden it was short in the front and long in the back. I got it that day. I ended up doing all my fittings in her studio, which was amazing, in Flatiron. She and her people tailored it for me, and they built the little T-shirt capelet thing with me.
Chris: At the time, I was a lawyer and was wearing a lot of suits, so I knew what I liked. I went to the tailor where I had all my suits made, a place called P. Johnson. It was a fun process to make the tuxedo because they take good care of you, and you can go in and build the details. There were some special little things we did, like the date of the wedding was embroidered inside of it.
Maddie: My shoes were pink glitter by Jimmy Choo, which I loved. They were very comfortable. Our flowers were magenta-y, a little bit messy. Our wedding planner, Melissa McNeeley, who’s amazing, said, “You have to meet Doan Ly. She is incredible.” And she is. Her whole team is all women. You have to follow her on Instagram. The Weylin is the type of place that could be really precious or stuffy if you did something too white. I just wanted to funk it up and make it feel fresh and cool. The flowers really helped with that, because they were beautiful but messy. Our candelabras were actually Lucite.
Chris: Right after the ceremony — this was our wedding planner’s idea — we got pulled aside into a little room and we just sat together with a cocktail and some appetizers. We hung out for a minute, the two of us, and it gave us a chance to just be together, basking. The night I proposed we were sitting side by side, too, at our kitchen counter. Her eyes popped out of her head and she realized why I was giving her a whole spiel about how much I loved her, and she said yes.
Maddie: There was a cocktail hour downstairs in the Weylin’s vault. It looks like an old library. The same jazz band that played during the ceremony moved in, but they added more people, a trumpet. I didn’t eat anything there, which was really sad. We had a raw bar, which I know people were really excited about. We love shrimp cocktail and oysters, and we had Negronis because we were drinking a lot of Negronis at that time in our lives.
Chris: I really just remember running around with a beaming smile on my face, shaking hands and hugging people and being like, “I can’t believe this just happened.” It was dreamy, and I was totally in love with Maddie. It was a plated dinner by the caterer, Abigail Kirsch, and we picked more dishes that we really love. The Weylin is across the street from Peter Luger and in a nod, we had a classic steakhouse-type meal, wedge salads. I think the food was good, but I didn’t eat more than one bite.
Maddie: At the last minute we added a chicken because my dad was like, “You need to give people two proteins.” Okay.
Chris: And my family’s food contribution was that we had an Oregon-themed gift bag in all our hotel rooms with these salted caramels from Alma in Portland, which we both love. They also hosted our rehearsal dinner at Vic’s in Nolita. My mom loves making cookies, so we had peanut-butter cookies from Ovenly that we gave away that night.
Maddie: His parents had given speeches the night before at the rehearsal dinner. My brother spoke, Chris’s best friend spoke, and my parents both spoke. I feel like I’ve been at so many weddings where just the bride’s dad gives a speech, and my mom was like, “There is no way. We are both speaking.”
Chris: We wanted everyone to sit and eat, so there was a great band, led by Benny Benack III, playing during dinner and then we transitioned to a DJ, Kenan. I basically said, “Do whatever you want, man, I love your music. Make it wedding appropriate.”
Maddie: Our first dance was “You Send Me,” by Aretha Franklin. We had a father-daughter, mother-son dance — my dad and I started dancing, and then Chris and his mom joined halfway through, so it was just one song. We aren’t dancers, we wanted to keep it quick! Then the cake was from this woman called Nine Cakes. We both didn’t eat any cake, but I’m gluten free, and it was a gluten-free cake.
Chris: Because we were basically married on Halloween, it was a little Halloween dark-chocolate cake. It was supposedly delicious. Everyone was dancing, the music was incredible, the bar was flowing, so we didn’t want to make a big thing of the cake-cutting. After a couple hours upstairs with Kenan, we went back downstairs to this speakeasy lounge thing.
Maddie: My brother DJ-ed the afterparty, and we were surprised by how many people went — everyone went, Howie and my parents definitely did, although I don’t remember if Bobbi stayed, actually. We had a ton of Halloween candy, then we ordered pizza.