Kelsey and Jon

How We Met

It is hard to pinpoint when Jon and I actually first met – we grew up together! Even though we went to elementary school, middle school, and high school together, it wasn’t until after graduation that our paths crossed and we became fast friends. We spent the summer before college inseparable and parted ways to attend different universities in the fall. After over a year of visiting each other’s schools (still just as best friends!), we both ended up transferring to UMass Amherst. Jon will say this is when he knew I was “the one”, but it took me a few more years to figure that out from my end.

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After college, we both moved to Boston and got jobs in startups. I work in HR and I was constantly gushing about the awesome new company I was working for. After much convincing, Jon got me to agree to let him come in for an interview. The team loved him and I ended up hiring him! We went from high school classmates to college best friends, to coworkers (on completely different teams, thank goodness). It was around this time that I came to the realization that Jon was more than just my best friend. We kept it under wraps for a few weeks while we went on dates around the city and then finally told our family and friends. The reaction from almost all of them was “um, duh!”, and both of our moms cried happy tears. That was 3 years, 3 apartments, and 1 very adorable chocolate lab ago. We’ve been together ever since.

How He Asked

I woke up on a cloudy Saturday ready for a full girl’s day complete with blowouts, makeup, and manicures appointments with my two best girlfriends. All of our guys are best friends, too, and it happened to be one of their birthdays, so the plan was to meet up for a nice dinner by the water in the city to celebrate that night. When we pulled up to the restaurant, I saw Jon standing there with our pup, Parker, standing next to him. That’s when I knew what was about to happen! He walked me over to the harbor walk where we used to walk Parker every night as a puppy, and he got down on one knee and asked me to marry him. Parker was a very good boy and sat next to Jon the entire time!

Next thing I knew there were two (amazing!) photographers next to us snapping our photos. They got some amazing shots that I will cherish forever. After a little photoshoot, we went to meet our families and best friends for celebratory champagne and spent the night dancing the night away with all of them. It was an absolutely perfect day.

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Special Thanks

CityLux Studios
Photographer