TerryAnn and Michael

Wedding Proposal Ideas in Acorn Street, Boston, MA

How We Met

Mike was the last person my then brand new boss introduced me to in the office after taking me on a small tour of the company campus. Mike didn’t work on the legal team, but our teams worked closely together on a pretty regular basis. I’ll never forget our first interaction. My boss and I walked over to his desk and he looked up at us with a big smile. We were introduced and my boss said: “he has the best socks in the office”. I looked down and sure enough, peaking out of the space between his pants and shoes were pink, blue and green socks. Mike quickly replied with “don’t undersell me, I also have the best smile.” To which I sarcastically responded, “and he’s humble too.”

Engagement Proposal Ideas in Acorn Street, Boston, MA

We didn’t talk or even see each other again until about a month later. I presented a project I worked on for my team and my boss suggested that it would help with a project Mike’s team was also working on. He recommended I send my work over to Mike who was heading that project for his own team. I e-mailed the work to Mike per my boss’ suggestion, and a few days later Mike was standing at my desk with a large chocolate bar to thank me for the work that I had saved him. At the time I was dating someone else and thought nothing of the gesture. Mike and I didn’t interact again for about a year.

My work BFF Jess worked on the same team as Mike. She and I ate lunch together every single day, and one day she invited Mike to join us. That first lunch with the three of us we chatted and laughed about everything. Soon Mike was eating lunch with us every single day. We talked about our relationships, dating, family, trips, all of the weirdly personal information work friends share with each other. When I went through my breakup Jess was there as a literal shoulder to cry on. It was through Jess that Mike learned I was single. Not too long later, unbeknownst to her, Mike asked me on a date. The rest is history.

TerryAnn's Proposal in Acorn Street, Boston, MA

How They Asked

Mike asked if I wanted to go on a little vacation to a city I’ve never been to before. He started showing me pretty places in Nashville, and Charlotte. We had traveled so much this year that I told him I was burned out and didn’t want to visit another new city. Instead, I suggested doing a stay-cation right here in Boston. He reluctantly complied but insisted we get a hotel and be “real” tourists. About a week or two later he asked me if I had ever visited Acorn Street. I wasn’t immediately familiar, but when he pulled up pictures I quickly recognized it as one of the most photographed streets in Boston. Being the amazing Instagram boyfriend he is, he asked if I wanted to take some pictures there for my blog. I was so excited and immediately agreed!

The day Mike asked me to marry him started with an extremely relaxing two-hour-long couples massage at a spa we had visited on his birthday the year before. It was immediately (and coincidentally) followed by my best friend in the whole world asking me to be her Maid of Honor. After accepting that first (MOH) proposal I turned to Mike crying and said: “this day can’t possibly get any better!” Not knowing that in a few short hours he’d be proposing to me lol.

After checking into our hotel we changed and headed over to Acorn Street to take pictures. Mike was being so weird that I honestly thought he was upset with me for some reason. We got to the street which was pretty deserted save a few stragglers. Mike began taking pictures of me and he was getting really into it. Towards the end, he was on the ground trying to get a really good angle. I was starting to become a tiny bit embarrassed so I went over to him to get the camera and see if he got any good pictures. Instead of handing me the camera, Mike reached into his pocket and said: “While I’m down here…”. I pretty much blacked out for the rest of the proposal.

All I remember is a sense of complete shock and utter disbelief, followed by an overwhelming feeling of joy. I was totally and completely caught off guard and blubbered like a baby for about 20 minutes. By the time I finally blurted out “YES!” a group of British tourists approached us and congratulated us. One woman from the group looked at us apologetically and said: “I know this might be a bit creepy but I took a picture of your proposal.” Another girl from a separate group of tourists had filmed a short video. I will forever be so grateful to these two people for capturing such an amazing moment in our lives.

I’ve never in my life been happier to answer any question. Mike is my literal dream guy. He goes out of his way to make me happy. He’s truly the kindest, funniest, most thoughtful and sincere man I’ve ever met and I’m so excited to spend forever with him!

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Special Thanks

Anderky Santos
 | Photographer