Dan and Ali | College Sweethearts Proposal

Dan and Ali College Sweethearts (40)How We Met: Dan and I attended the University of Michigan in Ann Arbor so maize and blue run deep through our veins. At the beginning of my sophomore year and Dan’s junior year, we met at one of our fraternity/sorority parties. Even under the influence of some college fun, we instantly had a connection. Both Dan and I were in other relationships at the time, but our friendship began to grow.

Ironically, our fraternity and sorority decided to partner up for Relay for Life, joining forces as one larger team. Since I was the lead for my sorority and only really knew one person from the fraternity, I asked Dan to co-chair with me. To this day, I still claim that I made the first move!

Over the year we quickly became goofy best friends as we raised money for our team. We parted ways for the summer and upon returning to Michigan in the fall we were both newly single. Although neither of us had any intention of diving into another relationship, we quickly realized we couldn’t be kept apart. For months we tried to fight our connection and stay just friends, having fun at times and bickering as best friends often do at other times. As our favorite quote states, “they stood there pretending to be just friends when all the time in the world could not pull them apart.” After a pretty typical college spring break in Cancun, we came home and never left one another’s side. Our best friend’s brother picked us up at the airport with a sign that read “Mr. and Mrs. Hassing” as a joke…who would have thought it would become true four years later?

Soon after our trip, Dan graduated and moved to Minneapolis while I stayed in Ann Arbor to enjoy my senior year. We made many visits to one another and Dan loved having a real excuse to continue living the college lifestyle and attend as many Michigan football games as possible. After I graduated, I moved to Minneapolis for work and we spent two years together there. We quickly became ready for another adventure and moved to Boston. We are beyond in love with the city and hope to never leave.

How He Asked: I knew the proposal was coming any day now for a variety of reasons. Not only had we designed a ring together, but I also had a few awkward run-ins with our family jeweler and had a feeling something was imminent. I am the planner of the relationship and it was killing me not having control. For weeks I did my hair and makeup every day and made sure to have a good outfit on since I knew a proposal was right around the corner. I tried hard not to think about it, but I was so excited I couldn’t focus on anything else and kept wondering how Dan would ever manage to surprise me.

The week leading up to our proposal was the last week before I reunited with all of my sorority sisters from college, whom I of course wanted to celebrate with. All week I joked with Dan about my ability to wait running out and simultaneously texted with my best friend from college asking her if she was coming to surprise me. They both had such great poker faces, Dan even started a fake fight the night before our engagement to throw me off and it definitely worked!

The next morning I woke up and met my friend for brunch. It was the first time in weeks I didn’t care what I looked like because I was going to the gym afterwards. Of course, this is when the proposal started! When I got to brunch, my now maid of honor had flown in to surprise me. After many tears and making quite the scene on a street corner, she handed me an envelope from Dan. It told me to have brunch with my best friends and come back to our apartment afterwards. He also gave me rules for the day, which included smiling, relaxing, and taking lots of pictures. This was the first of many letters throughout the day, which sent me on a scavenger hunt throughout the city of Boston.

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Each letter discussed a different aspect of our relationship and said he was waiting for me at the next spot. Then, the next letter always began with “you just missed me.” So, as the day went on, which included a slideshow of our relationship and a surprise visit from my sister, I never knew where he would be. However, Dan ended each letter with “I love you” so when the last letter read, “I will always love you” I had a feeling he would be in the next location. When I got to the Charles River Esplanade Dan was waiting for me and walked me to the center of a bridge over the water with the city in the background. As soon as he got down on one knee, I immediately started sobbing and the rest was a blur. It was the most incredible five minutes of my life that I have absolutely no memory of. Afterwards, a photographer popped up and preceded to shoot a proposal session with us. When we returned home, more friends were at our apartment with balloons, champagne and cupcakes. It was the most incredible day of my life. I can’t wait to marry my best friend!

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Photography by Makayla Jade Creatives