Alyssa and Jack

Proposal Ideas Our apartment in Greenpoint Brooklyn

How We Met

We met December 29, 2009. It was the anxious part of the year between Christmas and New Years where everyone is just waiting for something to happen. A friend from school, a fellow Meteorology major, invited me to a party. I agreed as I was home from college with little else to do. Jack had been invited to the party by the same, mutual, friend whom he had met at his freshman orientation. We’d never met before, but despite my late arrival we immediately took note of each other. I couldn’t ignore his neon orange hoodie and he couldn’t help but notice my friend and I were the only girls at the party.

Alyssa's Proposal in Our apartment in Greenpoint Brooklyn

Once we got to talking we found we’d had more than our friend in common. We had attended some of the same concerts, we’d both been at the same prom two years prior, and we were even going to have a class together in the next semester. This shocked me the most as it was a fairly small science course on a campus he didn’t live on. We began seriously dating halfway through the spring semester and have been nearly inseparable ever since.

How He Asked

We’re not sure the exact date I proposed but it was around the end of 2016. I was stressing pretty hard because I was about to turn 26 and lose my health insurance. While on the phone with my parents discussing my options a light bulb went off. Jack has insurance! I’ll marry him! When I brought this up to my parent they thought I was kidding, but I was already coming up with a plan.

It was difficult to think of a way to propose to my boyfriend of seven years. I decided I’d surprise him on one knee when he got home from work, tell him how he makes me a better person, and ask him. This did not go according to plan.

I heard Jack at the front door of our building so I got into position. But as I saw Jack walking into the apartment our roommate came in too. In the six months, we’d all been living together the two of them had never gotten home at the same time! So, flustered, I pretended to be picking something up off the floor. Once our roommate went into his room I pull Jack aside and whispered: “Can I marry you for your insurance?” Who says modern romance is dead? Jack said sure and we immediately began looking for a ring.

We were going to have to move quickly to make sure I kept being insured (I’m more than a bit of a hypochondriac) but we were sworn to secrecy as my older sister was going to be married in August. She would have killed me if I got hitched first. Less than a week after I proposed I got a call from work letting me know I was qualified for insurance in the following year. We were so relieved not to have to rush anymore. I joked that we could call things off and Jack could propose “for real” but he insisted that I had proposed, he accepted, and now I was stuck with him.

He also revealed that he had been planning to propose in a few months and had already begun looking at rings. He’d planned to ask while we were riding The Cyclone at Coney Island, but I have my doubts he’d have been able to hang on to the ring…