Ashley and Chance

Marriage Proposal Ideas in Boston, MA

How We Met

Sophomore year of college at University of Illinois Springfield, I was sitting in my biology lab with this goofball, Chance Simpson. As I got to know him, I found out he was on the baseball team (as I was on the volleyball team), and had the biggest heart. But, we started “talking” right before winter break. I did not do a good job of texting him during that break and you better believe he called me out on it once we got back to campus.

His best friend and teammate was dating my best friend a teammate and encouraged me to “give him a shot” because he “is a nice guy”. I did, and I’m so glad I did. Chance was actually my first (and now last) boyfriend. I prayed so much for my future boyfriend and husband, so I guess it was God saving the best for me.

We juggled being students, graduating, our athletic priorities, his professional baseball career and my move to Georgia. We started doing distance when he graduated in 2016. He was playing professional baseball all over the country and I was still in school. I got accepted into a masters program at University of North Georgia, so I moved 10 hours south to the beautiful Dahlonega, GA.

Those two years were rough, being apart, but we were both pursuing our passions. We grew a lot in those two years and also got to experience some pretty cool things. We traveled to Asheville, Charleston, Savannah, Atlanta, you name it. We also got into hiking since I lived in the foothills of the Appalachian Mountains. I found out that after I graduated I would be moving back to the Midwest, to Indianapolis. Still doing 4 hours of distance we are able to make it work and cherish our time together.

He is my person and balances out tendencies to be a little bit more uptight about work and school. Through all the distance, ups and downs and life changes, we’ve always been there encouraging each other to reach our potential.

Distance has been tough but I’m so thankful for all of the amazing places we’ve visited and memories we have because of it!

Wedding Proposal Ideas in Boston, MA

Ashley and Chance's Engagement in Boston, MA

Where to Propose in Boston, MA

Ashley's Proposal in Boston, MA

Engagement Proposal Ideas in Boston, MA

How They Asked

With my job I was able to take a professional development trip to any city of my choosing. I’m a Midwest girl and have never been to the Northeast. I decided Boston would be where I would travel too. I was doing business Wednesday through Friday, and on Friday Chance showed up (from Illinois) and asked me if I wanted to go out to dinner to celebrate our 5 year anniversary.

Unsuspecting at this point I said, “Sure!”. All he told me was to dress nice and he had the rest under control. Being a Type A I was a little reluctant but said okay. We get dropped off at the Boston Harbor and I see this beautiful yacht. Chance said, “That’s it, right there”! He had reserved us dinner on this yacht on the Boston Harbor. We got onboard and our table had a bouquet of roses for me to celebrate our 5 year dating anniversary. We took some pictures, drank wine and enjoyed our food. After we ate Chance wanted to go onto the top deck to get a view of the Boston skyline. I had just taken a video as we were taking in the view of the city and ocean, and he took both of my hands. At this point it took me a couple of seconds to catch onto what was happening. After his sweet words, Chance got down on one knee and asked me to be his wife.

He had coordinated with the photographer on board to catch the moment and afterwards we went back down to our table and celebrated with champagne and dessert!

We ended up spending the rest of the week enjoying Boston and celebrating our engagement, together!