Ashley and John

Wedding Proposal Ideas in Avery Bar in the Ritz Carlton Boston

How We Met

One night in my best friend’s hometown, we went out to a local bar called the Spruce Street Tavern. When we got there, I met a bunch of people, and it turns out that people in the town of Clinton love the name, John!

“Hi, I’m John.”

“Hi, I’m Jon.”

“Hi, I’m John.”

“Hi, I’m John.”

I thought it was a joke so I said, “Are you guys ‘punking’ me?” It turns out they weren’t!

There was one John that kept my attention even though he didn’t say much. We kept making eye contact from across the bar and I tried getting the scoop from his friends around him if he was single. He was! After having some (a lot) of wine encouragement, I confidently went up to him and asked if I could put my number in his phone. 20/20 hindsight, probably not the smoothest thing but hey, it worked out in the long run! I didn’t know at the time but he was his friend’s sober driver for the night. After not getting a text after I left that bar, I was convinced he thought I was crazy. After he was done driving everyone, I got a text that said, “Hey!” Naturally, I had to play it cool because he waited so long to text me so I said, “Who is this?” And from there, it was history!

Ashley's Proposal in Avery Bar in the Ritz Carlton Boston

John’s point of view: It all started out as another typical Saturday Night in my hometown. I was exhausted from plowing snow the previous night and contemplated just staying home and getting some rest. I probably would have if my best friends hadn’t guilt me into going out to the bar because I wasn’t able to hang out with them the night before. So, I decided I would be their designated driver and we made our way over to one of our favorite bars in town, The Spruce Street Tavern.

Ashley and John's Engagement in Avery Bar in the Ritz Carlton Boston

While there, a group of girls from town came in, as well as one particularly beautiful girl that I hadn’t met before – that girl was Ashley. After I said hi to her friends, Ashley came over to introduce herself to me and my four friends who I was sitting with at the time. I kid you not – we were all named either John or Jon. She really thought we were busting her chops and I don’t think she actually came to terms that that was all our names until some time after. As the night went on, Ashley and I kept making eye contact and small talk with each other until Ashley finally came up with the confidence to make the first move.

Engagement Proposal Ideas in Avery Bar in the Ritz Carlton Boston

She came over to me shyly and with some nervousness, and asked me if she could put her number in my phone. My immediate facial expression showed that I was in shock. Ashley later told me that she thought my facial expression showed that I was put off guard. But in reality, it was shock and happiness at the same time because I was trying to muster up the courage to ask for her number myself (can’t say I blame her for not being able to wait to make the first move). After that the rest was history and I became happier than I could ever imagine.

How He Asked

In the fall of 2017, John and I attended a friend’s fundraiser that supported cancer research. After buying some raffle tickets and putting most in a Patriots New Year’s Eve game bucket and a 2-night stay at the Ritz Carlton bucket, along with a bunch of other people, we were VERY shocked to hear our name be called as the winners of the Ritz Carlton 2-night stay. We weren’t sure when we wanted to use it but we thought it would be nice to use it on a long weekend so we would have an additional day of adventure around the city. I’m usually a planner and very time-oriented. This time, however, I did not want to be the planner. I told John that he can decide when we go and I’ll think of fun things we can do while we’re there.

In January, we decided to ask the Ritz Carlton if there was availability on President’s Day Weekend. My birthday is in January, our anniversary is on February 6th and Valentine’s Day is obviously on February 14th. We thought that President’s Day Weekend would be the perfect timing around all of these dates for us to celebrate our anniversary and Valentine’s Day, both of which were weekday holidays this year. We had very low expectations that it would be available because it was the start of school vacation week, it was a long weekend, we booked it fairly close to the date, and it was free for us – it just seemed like the chances of that weekend working out were slim. It turned out that they did have availability and we booked it for Friday night, February 16th and Saturday night, February 17th.

On Saturday, we booked a City Wines Tour that my sister and sister-in-law had given as a birthday present. The dress for it said business casual so we decided that we’d dress up a little spiffier than we normally do. One of our FAVORITE things is going on date nights and adventures so, this was just another adventure in our eyes.

The wine tour went from 3-5: 15 pm. After, we went back to the hotel to relax until dinner (which was a surprise as to where we were going to go). Our relationship has been full of little surprises and planned date nights so this was not really out of the norm. We got back to the hotel and I stopped in the bathroom while John went to save us a spot at the couches by the fireplace “to make sure we could get a seat.” The night before when we walked by there, it was very crowded and I really was hoping we could get a seat by the fireplace on the comfy couches. When I walked from the bathroom to the lounge area, I realized that there were plenty of open seats even though John was already there holding our spots.

The pianist was playing in the background while we ordered drinks. I ordered a glass of red wine and John ordered a beer. When the waitress left, John and I were just talking a little bit and he grabbed my hand with one hand and used his other to grab some of the free peanuts. When he grabbed my hand, I said, “Why are your hands so sweaty?” not really picking up on anything. John’s response… “The fireplace is making me hot.” Now looking back at it, that was very clever.

The pianist’s song had just ended and a new one started. John said, “Do you hear the song??”

Ashley replied, “Umm I hear the instrumentals.” And then the words started. It was Elvis Presley’s song, Can’t Help Falling in Love. This is a song that we have danced to so many times before and it’s the song that always makes us think of one another. When I finally heard the words, tears instantly started flowing and I knew exactly what was about to happen.

John got down on one knee with the biggest smile on his face. At that moment, the time had frozen and I couldn’t stop smiling knowing I would get to spend the rest of my life with my best friend and soulmate. When he finally got up, we danced to the song but this time as fiancés.

Everyone in the bar area clapped for us and came up to congratulate us when the song had ended. The Avery Bar sent over congratulatory champagne and John and I got to toast to each other.

John had everything so planned out, thought-through, and perfect and I still get goosebumps thinking about that night.

Special Thanks

Zachary Trombley
Planning