A Rooftop Wedding With Questlove As DJ

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 macaroon towers, how to see beyond the usual tropes and actually pull off a non-cookie-cutter affair? For the answer, we’ve decided to interrogate the cool couples whose weddings we would actually want to steal — right down to the tiger-shaped cake toppers.

Here, we talked to Samantha Shipp and Demetrius Warrick, two lawyers (she as general counsel and COO of an investment company in Rwanda, he in mergers and acquisitions) who met at the University of Michigan but took over a decade to find themselves in a relationship. They were married on September 16, 2018, in a rooftop garden overlooking St. Patrick’s Cathedral and Rockefeller Center — and with Questlove as their DJ.

Sam: I love a project, I love a theme — gimme a theme and I am just going to crush it. I had been to a birthday party at 620 Loft & Garden ($12,500 for space rental) — it’s dope because you’re having a picnic basically on top of the city, on top of Rockefeller Center — and it also had this indoor space, completely white, like a museum, that you can make it completely your own.

Demetrius: Any type of creative endeavor, Sam is going to take it and run with it.

Sam: When we looked at the venue in June 2018, they had no Saturdays left for the year, but I was not mad at a Sunday. We locked in the date for three months later. I figured, if I’m ready to get engaged, I’m ready to get married. We wanted to do it while it was still warm. I designed the Save the Date video myself on my phone, perhaps my only cost-cutting measure. And my very next thing was to call Camille Russler — a celebrity stylist that a mutual friend had introduced me to years prior — and fly down to her bridal shop in Miami. She pulled stuff for me. I wanted to feel sort of casually glam, like, Oh, I just showed up here looking better than everyone else. I thought for a day and pulled the trigger on a Vera Wang (Fontaine gown by Vera Wang, $15,000). For Demetrius, everything was custom from the Harlem Haberdashery ($3,000).

Demetrius: I thought off-white or cream was pretty clichéd, so my idea was to go subtle and navy, not play it too big. Then I was like, the hell with it, you only get married once. I asked the tailor: “Can we get pictures of us put inside the lining?” And he said absolutely. It was this very elaborate collage inside the lining of the jacket, and it was executed to perfection.

Sam: I knew he was planning that, but he picked all those photos of us and I didn’t see it until the wedding day. We’d known each other since 2006, when we met at a house party in Ann Arbor; I was in law school at Michigan and he was applying to law school, so we had a law school conversation.

Demetrius: “Timing issues” is a really generous way to put it. We lost touch, primarily because, you know, I pulled a dick move. She reached out, I pulled another dick move, we’d lose connection. Finally, in March 2017, she sent me a text calling me a loser. We’ve been together ever since. Everything about her is what I would want in a wife; it took ten years to figure out what that actually meant for me.

Sam: We wrote our own vows. It was actually the most important thing to me about the wedding. When I go to weddings and people don’t do their own vows, I’m so disappointed. Like, why am I here?

Demetrius: Our dog Seven was the ring bearer. He had the rings around his neck.

Sam: I had six bridesmaids, he had six groomsmen. I just asked them to wear long navy dresses; I didn’t care about the style. Johanna Rollins did the bridesmaids’ makeup ($250 each); Camara Aunique did mine ($2,750). Dailey Green of H2 Salon in Brooklyn did my hair ($350) and her colleague Adia Braz did the bridesmaids’ hair ($300). They came largely ready and then Adia did a little assist. The bridesmaids carried actual 1960s church fans with MLK on them that I found on eBay, instead of bouquets. The groomsmen wore Aretha Franklin pins, because she had just passed. The idea was the women carried King, and the men wore the Queen. For the rest of the guests, we had fans made with our picture on the front.

Demetrius: The old-school black church fans would have pictures of Jesus on them, or some figure like MLK or JFK, so we re-created that idea. The ceremony was outside and we knew it could get humid. The program for the day was on the back.

Sam: The ceremony was outside and all of the dancing was outside. If it had rained, we would’ve been screwed completely.

Demetrius: We did not have a backup plan for rain. We’re not the most risk-tolerant people in the world, but my perspective was, listen, if it rains we’re either getting married in the rain, which I was totally okay with, or we’re going to find a way to convert the inside space.

Sam: In terms of the decor — originally I wanted to turn the space into an art gallery with images of black love; I was working with an artist on it, but it just didn’t work out. So we kept it simple, with a big floral arrangement at the head table and smaller pops on the other tables. (Florals by Marjeth Cummings, marjeth1@optonline.net, $9,150). We asked our 120 guests to arrive at 5 p.m., but the wedding ceremony wasn’t actually starting until 5:30. I think it’s important to just say that it was a black wedding, just super black, and people that don’t normally show up on time — they did. Because I lied to everyone: I told them it was starting a half hour earlier and we were closing the doors so they couldn’t get in if they weren’t on time. So that seems to have worked.

Demetrius: During cocktail hour, a DJ started. Our DJ was Questlove.

Sam: That was a favor! We’ve been friends a long time. He sent me his calendar, and I found a day when he was not working. Our hashtag was #MotownPhilly2018 — I’m from Detroit, Demetrius is from Philly — and he was in the original video. I was just like, “This makes sense. I need you to do this.” I really didn’t know up until like maybe a week before that he was for sure doing it.

Demetrius: That was massive.

Sam: Quest, God bless him, DJ’d the entire night. People were taking selfies with him. Our first dance was “Really Love” by D’Angelo. I worked on that album when I was still practicing entertainment law.

Demetrius: We changed while everyone started dancing. I don’t know how familiar you are with Dapper Dan? Harlem legend, clothier, he dressed everybody in hip-hop all over the globe over the past 30 years? We got Dapper Dan to create outfits for us.

Sam: The Dapper Dan outfits looked like black excellence. He has a partnership with Gucci, and there has been a lot of controversy with Gucci and the black community the past couple months; our wedding predated that, but anyway, we weren’t really interested in wearing Gucci. We were interested in wearing Dapper Dan. Getting to sit down with a legend like Dap and actually collaborate on a design with him was a highlight of the wedding planning. (Sam’s bolero jacket, $2,300. Sam’s pants, $1,350. Demetrius’s jacket, $3,200)

Demetrius: They told us they had never dressed anybody for a wedding. It was rocks off for the rest of the night.

Sam: Whatever our budget was, I blew it. The total cost of the wedding ended up around $120,000. It was $24,000 for our caterers, Purslane. But actually that was more cost-efficient than going with one of the all-in packages at 620: My wedding planner, Leah Weinberg of Color Pop Events, did the math for me, and she said you can pay me and you can pay an outside caterers for less money than the 620 catering option will cost you. We served a watermelon salad to start, then a sea bass in banana leaves or chicken breast. Our cake was by Keremo Cakes in New Jersey ($1,000), white, very simple, with tiers in red velvet or oreo filling. We also added some other items; there’s a restaurant in Detroit, a staple called Coney Island, that makes chili-cheese hot dogs. We got them to make mini dogs, and then we had little, bitty cheese steaks because obviously that’s what they do in Philly.

Demetrius: Honestly, we didn’t eat much at all.