Skyler and Sebastian

Marriage Proposal Ideas in New York City, Upper East Side (rooftop of our building)

How We Met

Sebastian and I met on New Year’s Eve, December 31, 2015. He was my New Year’s Kiss, and the rest…is romantic and extremely unconventional history. Right before we met, I first of all, almost didn’t go to the New Year’s Party because I was feeling exhausted, and second, I had sworn of dating and promised to focus on myself going into the new year. Well, neither of these things happened, as I ended up not only going to the party, but meeting my future husband! Sebastian and I still debate on who said hi to who first, but we had both been watching each other and waiting for the perfect moment to introduce ourselves. Within the first five minutes of talking to Sebastian, I knew he was the one. A once anxious dater, I felt this overwhelming sense of calm and that I could finally just be myself. We spent the entire night making jokes, laughing and having the best time with our extremely weird senses of humor.

At the end of the night, we kissed, and I left to go get late night pizza while he went to the after party looking for me.

Seb and I fell head over heels for the next three months. I loved his creative approach to “courting” me, as he would say. On our first date, he took me to dinner on the Upper West Side (dinner first dates in NYC are almost unheard of these days, so this was really special to me.) Our next dates were even more fun — we went to the Lunar New Year Food Festival, the Bronx botanical garden and Little Italy, and an authentic Filipino brunch — to name a few. Everything about him was right for me — I knew he was my person, but he had just gotten out of a rocky college relationship and was nervous things were moving too fast. We went our separate ways. I was upset, but little did he know, I already loved him and wanted him to be happy, so we spent 6 months apart. In the fall, he asked me to go to a medieval festival (a true Sebastian date choice,) and it was the start to our new beginning. Through awkward laughs and turkey legs, we discussed our potential relationship.

After 2 months of seeing each other again, Sebastian asked me to be his girlfriend while playing games at Dave & Busters. We celebrated by going to Korea town for some karaoke, and then, the rest was history. Since that night, we’ve been on countless adventures, got a dog, got engaged, and now are moving abroad to London to start the next chapters of our lives.

Proposal Ideas New York City, Upper East Side (rooftop of our building)

Wedding Proposal Ideas in New York City, Upper East Side (rooftop of our building)

How They Asked

Talk about the best birthday EVER. My wish came true before I even got to make it! Sebastian surprised me on my 26th birthday with the most romantic and beautiful proposal, and oh…the most gorgeous ring I’ve ever seen! Every year, Sebastian and I go to dinner for my birthday, and this year, he told me he would meet me at home at 6:45 to change quickly and then go to the restaurant. When 6:45 rolled around, he called me and said he was almost home, but that our doormen left a package for him outside our door and asked me to go pick it up quickly. I opened the door and there was a package on the floor that said “My Love.” My heart began to race as I thought I knew what was happening, but I was also unsure, because it could have just been a birthday gift. I was still on the phone with him when I opened the package to find cupcakes and a card. The card said “Meet me on the Roof.” Naturally, my first question was, “Do you want me to bring the cupcakes?!?!” At first, I thought he was just going to surprise me with wine and we would eat the cupcakes. He told me not to, so I just went up to the roof cupcake-less and I had a feeling about what was happening.

Engagement Proposal Ideas in New York City, Upper East Side (rooftop of our building)

My heart was racing as I walked outside and saw a single rose. I followed that rose to find a whole path of roses and candles leading up to Sebastian in a suit in front of a table with a bottle of champagne and two glasses. I was so shocked and excited that I ran and gave him a kiss. Before I move forward, something you must know about Sebastian and I is that we balance each other out very well. I’m the romantic and intuitive — I believe in energy and the power of the universe — while he is much more logical and fact-driven. So when he began to tell me about how before he met me, he never believed in any of these things and how being together is the best thing that’s ever happened to him and meant to be, it made my heart beat 100239219031 miles a minute. He continued to speak from his heart, and eventually, he got down on one knee and asked me to marry him. I’m already shocked to my very core, and then came the next surprise. The ring. Another thing you should know: I had been looking at engagement rings for fun and thought I knew what I wanted (round solitaire, or something octagonal) but I wasn’t sure. I sent these pictures that I saw on Instagram to him a while back telling him this is what I wanted, but in my gut, I really wasn’t sure of what I wanted. I had no idea! I secretly wanted him to pick out something even better. And he did. He picked out the most gorgeous radiant cut diamond ring I had ever seen, I swear I almost passed out. I later learned that he had been spending months going to the jeweler after work to learn about diamonds and look at different ones so that he could pick the best ring. This radiant cut diamond ring is beyond anything I ever could have wanted to symbolize our love and our future marriage.

Skyler's Proposal in New York City, Upper East Side (rooftop of our building)

Sebastian put so much thought, time, effort and emotion into this proposal, and it was the perfect way to kick off our life together. The crazy thing is that it will only get better and more beautiful from here.

Skyler and Sebastian's Engagement in New York City, Upper East Side (rooftop of our building)

Where to Propose in New York City, Upper East Side (rooftop of our building)

Special Thanks

Yvonne Yuen
Photographer