A Lesbian Flag Inspired Rooftop Proposal in NYC
A rooftop in New York City, pink and orange florals inspired by the lesbian flag, a hidden ring, and perfectly timed Bravo tickets. Stella’s (she/her) proposal to Ariana (she/her) was thoughtful, theatrical in the best way, and deeply personal. It unfolded on the roof of their first apartment, a place layered with memories, intention, and a slow burn romance that started years earlier.
A Lex ad, Bravo bonding, and a lockdown slow burn
Stella: I was commiserating to a friend at The Woods about not meeting any femmes I connected with when they showed me Ariana’s Instagram and promised to get us in the same room someday. The very next day, completely coincidentally, Ariana responded to my ad on Lex. I usually did not reply to private accounts, but I recognized her tiny profile photo and remembered how beautiful she was.
We went on our first date in December 2019 and immediately bonded over Bravo, femme fashion, and niche internet celebrities. When the world shut down in March 2020, we were still casually dating and living with our families. I threw Ariana a very elaborate Zoom birthday party, and our daily FaceTimes brought us closer, laughing for hours at a time. By the end of that summer, we were falling deeply in love. We like to say it was a slow burn, made sweeter by lockdown. We moved in together in 2023, and it still feels like a slumber party with my best friend every night.
Why our rooftop felt like the only choice
I picked our roof, with beautiful views of the city. It is the first apartment we lived in together, and it holds so many of our early memories. It felt natural to choose a place that is already so special to us.
How an Etsy witch saved the day
Ariana and I had been designing our rings together and knew we wanted to get engaged this summer, but we could not figure out how. When we saw that her favorite housewife, Heather Dubrow, would be on Watch What Happens Live on August 14th, I had my plan. A sunset proposal on our roof, then a campy celebration at the taping.
There were a few hurdles. Ariana was flying home from Chicago that afternoon, and her ring was still in production. I asked Alexa Peretz Events for help, and she quickly brought together photographer Sylvie Rosokoff, florist Emthurium, and Chef Thabo (who was secretly cooking in my dad’s apartment). I envisioned pinks and oranges inspired by the lesbian flag, champagne, and a summery meal.
Rain was forecasted, so I paid an Etsy witch for a good weather spell. Yes, seriously. The sun came out anyway, the ring was ready in time, and everything aligned. I pretended I had locked myself out on the roof, “I Love You Always Forever” by Betty Who started playing, and we both immediately started crying. After she said yes, we popped champagne, ate a seafood forward feast and cake from Bodega Cakes, and a few hours later we were sitting in the audience at Watch What Happens Live, talking about the proposal on air.
Nerves, suspicions, and a very obvious yes
I was so nervous. I thought that because I was the one proposing, I would feel calm and in control. Instead, the second Ariana walked out onto the roof with me, I immediately started crying. She looked so beautiful, and in that moment I felt completely ready to ask her the biggest question of my life.
Ariana: I had some suspicions that Stella might propose that day, especially since we were going to Watch What Happens Live, but she kept throwing me off the trail. So when she asked me to come up to the roof before our “dinner reservation,” I was completely stunned. I could not believe how beautiful everything was. I felt so loved, so special, and completely ready to say yes.
Designing rings that felt like us
We designed our rings together at L and L Jewelry, which came recommended by my friend Marla, a fellow native New Yorker. They were a dream to work with, and the whole process felt collaborative and personal from the start.
Even though we designed them side by side, I picked up Ariana’s ring myself so she had never seen the finished piece before I proposed. For my ring, I chose four side baguettes on each side as a nod to Ariana’s birthday, 4/4. Our rings complement each other beautifully, but still reflect our individual styles. She proposed back to me two weeks later in Italy, which is a whole other gorgeous tale.
Stepping into this next chapter together
Getting engaged has felt invigorating and exciting, like we are stepping into a new chapter with real intention. We are both deeply committed to building a life filled with joy, laughter, and adventure, and saying yes to each other has only strengthened that.
I also still cannot believe I managed to surprise Ariana. We are so connected and share everything, so seeing her genuinely stunned was exhilarating. At the same time, engagement has reminded us how important it is to prioritize each other and protect quality time together, especially as the flurry of wedding planning begins.
Venue hunting and trusting the process
Wedding planning has been a little overwhelming, but also so fun! We are still at the very beginning, focusing first on finding the right venue and starting to shape what this celebration will look like.
The internet can be intense to sift through, so we feel really lucky to be working with our planner at Alexa Peretz Events. Having someone we trust to help narrow things down and zero in on the best plan for us has made the whole process feel much more grounded and manageable.
Capturing the moment and Ariana’s beauty
I knew I wanted to capture the proposal, and honestly, I wanted to capture Ariana’s beauty in that moment. It felt too special not to document.
Alexa reached out to Sylvie Rosokoff, and I was immediately obsessed with her work. She even did a walkthrough with me a few days before the proposal so she would know exactly where to hide and how everything would unfold. During the shoot, she guided us in a way that felt natural and easy, helping us feel completely relaxed and, yes, gorgeous.
Choosing vendors who reflect our values
We are both fervent researchers, so naturally we have been deep in the spreadsheets and tabs. At the same time, we are really trying to trust our planner and lean on her guidance as we build our vendor team.
One thing that feels non negotiable is prioritizing women owned, LGBTQ owned, and people of color owned small businesses. We want our wedding to feel like a love letter not just to each other, but to our community. The people we hire will be such a meaningful part of that.
Captured by Sylvie Rosokoff
Caterer Chef Thabo
Cake Maker Bodega Cakes
Dress Designer RIXO
Engagement Rings L and L Jewelry – New York
Florist Emthurium
Planning & Design Alexa Peretz Events
Rental & Decor BBJ La Tavola
