Amber and Leo

Amber and Leo's Engagement in My rooftop during a Halloween party

How We Met

I met my fiance, Leo, over twelve years ago through my sister. He was my sister’s boyfriend’s best friend. I’d sometimes accompany my sister to her boyfriend’s house, and my now-fiance would be there. We didn’t have much interaction then, as he was older, (I was a freshman in high school and he was a senior.)

Fast forward to my freshman year of college, and my sister mentioned that Leo was now single. I was single too, and feeling a little lonely since I’d never had a steady boyfriend in high school because I was focused on my studies. She put us in contact, and we connected via Facebook.

We took a Jamaican dance class for our first date in 2010, and I was quite terrible at the class, but it certainly broke the ice. We went for Japanese food after. It was the perfect mix of spontaneity and romance. We’ve been together ever since. He is my best friend and my total opposite. He’s an actor, people person and energetic, and I’m a book editor and introvert who loves to read and write. But, somehow, it works. We know how to balance each other out, and he’s always been my greatest supporter, and the best listener anyone could ever ask for. We are also both creative types and adventurers (whether it’s exploring NYC, drawing together, going to music festivals, or exploring Cuba), so we love to tackle new things and travel together, so that things are always fresh.Ultimately, I am just SO excited to be getting married to such a wonderful, caring, intelligent, thoughtful and hilarious person!

Engagement Proposal Ideas in My rooftop during a Halloween party

How He Asked

We got engaged during our Halloween party. Halloween had always been special to us. For the first birthday I’d spent with him, we went to a haunted house called Blood Manor, and we always liked to attend the Halloween parade in NYC. We’re also lovers of creepy things, and have many skulls throughout our apartment. Black also happens to be a fixture in my wardrobe and my favorite color, so it’s no surprise that he thought to propose on Halloween–except that it totally was!

I had been expecting a proposal all year. We had talked about an April Fools proposal because it would be hilarious, but that date came and went. Then, we talked about a summer proposal, but we traveled a lot this summer, so that was put on hold. I had started to think it would happen in late November. He told me he ordered the ring in September, and being that it was custom designed, it would take six weeks to deliver. I was sure the proposal would happen after my November birthday. But, boy, was I wrong. Little did I know, he already had the ring, and had been thinking of the best way to propose with the help of my sister, and a little help from one of my best friends. And, my sister, had the best idea: why not propose at the Halloween party Leo and I had already planned!

My sister had all been conspiring the week before my Halloween party. And, Leo dropped hints that the proposal would come in the next couple weeks by telling me to save a date for something special. I relayed this info to my friend, sister, and mother, and they pretended to be upset with him about being so obvious. I had no idea they were in on the plans. My sister even forced me to get my nails done “for the party”, which I give her great thanks for, because I am very difficult to get into a nail salon! (I’m not exactly a fan of manicures.)

So, on 10/28/17, at my Halloween party, Leo and I are playing Cards Against Humanity with our guests and having a great time, when my mom, (who is babysitting my niece in my bedroom– I found this strange because she has her own home, but I digress) calls me into the room to find a show for her on Netflix. I also thought this was strange, because she knows how to use Netflix, but I indulged her for a few minutes before I excused myself back to the living room to continue playing the game. When I returned to the living room–everyone was gone! The music had stopped and the lights were turned on. I was totally confused.

I went back into the bedroom where my mom, sister, and niece were, and told them about my missing guests. They acted surprised and suggested we go find them. At this point during the party, I had had a couple glasses of sangria, and was not as suspicious as I should have been, and agreed to go look for our guests. My mother, sister, baby niece and I went to the elevator, and we ended up on the 10th floor of my building. I turned to my sister, and asked why we were there, and she said it was fine. Not understanding, but wanting to find my guests, I followed my mom and sister, out to our rooftop terrace, where the floor was lined with flowers and candles.

Out on the terrace were all of my guests! They were holding candles too. And, there was Leo, in the middle of the rooftop. At this point, I knew what it was, but I still had my doubts. He did the proposal thing, and I said YES! I followed saying yes, by saying “You better be serious”, in case there was a chance it was a Halloween prank. Indeed, it was not.

I am engaged now, and I wouldn’t have wanted it any other way. It was beautiful, quirky, and wonderfully unique and I’m so glad that my family and friends got to share the moment with me! Now, we just have to start the wedding planning, but not before we enjoy our time as a finally-engaged couple.

Our Video

Watch more proposal videos & follow @HowHeAsked on Instagram for more stories!