Ashley and Tommy

Marriage Proposal Ideas in New York City, Village Cinemas

How We Met

Freshman year of high school I had Biology with Ashley gram. She was a year older, cute, and I tried to play it super cool all year. Well, end of the year comes, and Ashley signs my yearbook “ It was great getting to know you, enjoy the rest of high school!” and never spoke a word to me the rest of high school.

The first day of summer after my sophomore year of college I was hanging out in a friends basement when she asked if I remembered who Ashley Gram was because she was coming over. Well, Ashley walked in, and I opened a bottle of wine for her. We started talking and an hour later I had a date. Fast-forward a week later, we go on the WORST first date imaginable. We went to see Pirates of the Caribbean 4 at maybe 3 in the afternoon and upon leaving I kind of maybe sorta went for a kiss that she wasn’t looking for, but a half of a kiss was still a win in my book. I really liked this girl. 7 years later, we’re getting married.

Ashley and Tommy's Engagement in New York City, Village Cinemas

How He Asked

I always knew I wanted to do something big enough that Ashley deserved, but also intimate enough that it could be just us. As a video editor, that always meant it was going to somehow involve video. About a year before the actual proposal on a long drive I heard a Peter Gabriel cover of David Bowie’s “Heroes” come on. I knew almost instantly that this was it. I listened to that song 613 times leading up to the final edit of this video.

Over the next year, I would gather pictures, clips from Snapchat, Instagram posts, I also pulled a bunch of video clips featuring things that were really important to us through our relationship. I went and filmed locations like our parents’ houses, restaurants, the movie theater where that awful first date was. Our friends and family were even willing to lend me a hand and were all INCREDIBLE about keeping the secret too. I rented out a theater in the east village, but I had to get her there without her knowing. I was waiting outside her office with her favorite bottle of wine when she walked out.

So on a cool night in November we sat on a bench in Madison Square park drinking a $90 bottle of wine out of the free plastic water cups from Shake Shack (I forgot glasses, watch the lights come alive in the city around us. I told her we were going to dinner, but the reservation was really late, so naturally, a stop at Joe’s Pizza on 14th was the move. After a quick appetizer of our favorite pizza, I led her up the street toward our nonexistent sushi dinner. Once we passed the theater, I had to pull her inside quick before she could realize something was up. I grabbed popcorn and diet coke for her and led us right down to theater 2. The lights went out, the video played, and when it was finished the lights came up, and I was one knee next to her, ready to spend the rest of my life with my favorite person. She said yes (obviously) then we went a block over to a bar where our parents and friends were waiting to celebrate with us.

If anything could ever go as perfect as you could imagine, It was that night.

Our Video

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