Jennifer & Timothy

Jennifer & Timothy

December 7, 2024 • Sterling, MA
Jennifer & Timothy

Jennifer & Timothy

December 7, 2024 • Sterling, MA

Our Story

Our Story

Tim and I first met back in 2012, when my aunt Barbara set us up on a blind date. We went to Mulligans mini golf first. Tim learned on this day how terrible I am at golfing! After minigolfing, we went to Barbers Crossing. At the end of the blind date, Tim and I went out separate ways. We kept in touch over the years, but did not continue dating. A few years later, Tim and I went to Water Country together. We had a few laughs on the car ride and talked about life.


In 2020, I had reached out to Tim to see if he still had his motorcycle. I had purchased one in 2019 and wanted to see if he would like to go for a ride together sometime. As a new rider, I was nervous to be on the roads by myself, but knew that Tim would allow me to learn without judgement. We spent all summer riding around taking back roads and usually these rides were followed by grabbing lunch! We found ourselves spending more and more time together on the weekends and even sometimes during the week. We had spent hours having meaningful and honest converstion about our past and what we had hoped for the future.


In September 2022, I had begged Tim to go on vacation. After a little convincing, we booked a trip to Florida to spend 2 days at Universal Studios and 2 days at Disney parks. We had rented a place to stay about 20 minutes away from both parks that allowed us to have separate rooms, but shared living space. Our first night, we booked Universal Studio’s Halloween Horror Night. As for anyone who knows us, we both love Halloween. On that vacation, we had an amazing time. We spent the entire trip laughing, wearing matching outfits, and having the best time of our lives. On one of the last days on the trip, Tim and I went on The Tower of Terror. On the way down, Tim tried to hold my hand. Although confused, I was not upset by it.


On October 7th, 2022 Tim and I decided we needed to have “the talk.” I had picked us up dinner at Barber’s Crossing and while waiting for the food, I called Kiss 108 for the “what makes you smile” segment. I had explained that I was excited to take things to the next step with my best friend. Shortly after hanging up the phone, I called Tim and told him to tune to the radio so he could hear me! We had a long talk about how we should take our relationship from being just friends to being in a relationship.


In December 2023, Tim had asked if I would be interested in going to Tower Hill Botanical Gardens in Boylston to see the lights. After letting him know that I would love to go see them, he went ahead and booked tickets for us to go together on December 14th. When Thursday came, we were both getting ready to leave the house. Tim was dressed up wearing nice jeans and a Carhart jacket. As for myself, I had sweatpants, thermals, a winter hat, gloves, and two sweatshirts that I normally do not leave the house in. Tim of course asked, “Is that what you are wearing tonight?” I replied, “Yes, it is cold. It is not like we are getting engaged or anything.” Tim of course laughed, said “nope,” and walked away. Tim and I went through the garden looking at all the light displays and frequently stopped to take photos in front of them. We went into this one beautiful glass greenroom. I stopped and mentioned that it would be a very night space to have a wedding. Tim had mentioned we should ask someone who works there and find out more information on the space. We took a short break from the cold and ordered hot chocolate, a Reese cookie, and an apple cider donut. During the snack break, we had seen a women who works there and asked about the space for weddings. She had given us a card with the wedding planner’s information. We laughed as at this moment because we were not engaged. We went outside one last time to take a photo in front of the lights. Tim asked a woman to take our picture. Tim got down on one knee and before he could even ask, I started to ugly cry and said “Are you serious? Are you serious? YES!!” We both were flooded with emotions and excited to share our amazing news with our family!