Amanda and Jason's Romantic Rooftop Proposal

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How We Met: If you can think back before the world of online dating apps, there were few options available to meet people. You could meet through friends, meet randomly at a bar, or sign up to be on one of the paid sites such as JDate or Match.com. Back in May 2012 a brand new startup launched with a crazy idea to pair matches of people using friends-of-friends on Facebook. The startup was none other than Coffee Meets Bagel. At the time I was working at Techstars, a startup accelerator program in NYC, and had my pulse on the startup scene. My boss had asked me to sign up for this new dating site so he could check it out first-hand without having to be on it himself (he was taken!). Reluctantly, I signed up and thought, “hey, why not, there are likely a bunch of other tech-related people on here since it’s so new, it’ll be good for networking at the very least!” Coffee Meets Bagel pairs you every day with only one new match, exactly at noon, and you have to either accept or reject. After rejecting Day 1, on Day 2 I was sent Jason as a match. I saw we had 10 mutual friends, he had gone to Emory University, grew up in Philadelphia, and worked in tech – all very familiar things to me. I figured I would give him a chance and decided to accept. Jason on the other hand, had been on Coffee Meets Bagel for about a week or so already and had yet to find any girl worthy of accepting – I was his first! We started texting and immediately cut right to the chase of planning a date for that Thursday. When Thursday rolled around, I had tried to cancel a few times by saying I had to stay at work late, but late was great for Jason and his work schedule. He insisted we still meet. At 10pm we ventured to our first date spot at Stanton Social on the Lower East Side in NYC. We quickly bonded over drinks upstairs and made our way downstairs for late night bites. Hours flew by in what felt like minutes and the next thing we knew the restaurant had turned the lights on. It was 1AM and we had closed the place down! Jason, being a gentleman, dropped me off right in front of my apartment, we kissed, and said goodnight. The rest was history…

How He Asked: Jason had been trying to figure out the perfect way to propose to me, someone impossible to surprise, for months and months. With our three year anniversary approaching, he knew it had to be then. I had always known that it would be sometime around our three year mark together that we would get engaged, but I had completely ruled out that exact weekend since there were so many of my family members “unavailable” that weekend to celebrate and it was the weekend of my UPenn 5 year reunion. Our three year anniversary was on that Sunday, so when Jason had asked me to come back from Philadelphia on Saturday night, instead of Sunday morning to celebrate, he had to have a good reason. He told me he had worked hard to plan a fancy dinner, bought tickets to a show and that he had booked a helicopter ride for Sunday AM which started very early in the morning. These types of things were typical for Jason to come up with, so I didn’t think much of it and agreed. I returned back to NYC around 6PM and proceeded to take my sweet time getting ready for our 8:30PM dinner reservation, as Jason just sat on the couch as if nothing was up. As 8PM rolled around, Jason asked me to come up to the roof with him for a drink before dinner and to exchange the gifts we had gotten for one another. Also being a typical thing that we do, I went along with it. When I got to the roof and opened the door, it was pouring rain outside. Jason anticipated the potential of rain that night, and grabbed a beautiful white umbrella that was seemingly “left there” in the hallway and led me outside. Waiting outside was a walkway filled with hundreds of rose pedals, and an arrangement of candles on the ground and lights hanging in the trees.

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With the NYC skyline in the background, the site was truly breathtaking. Jason pulled out the card he had gotten for me. The card was the exact same card I had mentioned to him, over a year ago, that I wanted as my thank you cards when we got married – a card with our names and an illustrated picture of our faces. Jason began to read me the card and when he got to the end he got down on one knee and read: “We always say always and forever but there has always been one thing missing, Amanda Bari Bensol will you marry me?”

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In complete shock and excitement I screamed… YES!!… and reached down to kiss and hug him. I then realized the whole thing had been video taped and photographed as a photographer came out from behind the corner. Jason led me out of the rain, back downstairs to our apartment telling me we’d see our families soon when we get to the restaurant.

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When I opened the door I saw both of our families there waiting with a champagne toast – I was so excited! We all celebrated for a few minutes, and then they all started to rush me telling me we’d be late for our dinner reservation. Still thinking we were actually going to dinner, I got in the elevator obliviously. When the elevator stopped at the 2nd floor and not the lobby, I looked back at Jason with a huge smile. He led me into the event space in our apartment building where I saw an overwhelming amount of our friends and family waiting with hugs, and lots of love! A huge party was set up with amazing decorations, a full bar, BBQ, and a crazy dessert table. We partied all night long with everyone, in true Jason and Amanda style…

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