In 2014, Sydney and Caleb were both in New Hampshire volunteering for an organization called Generation Joshua. Their job was to encourage people to vote in the upcoming presidential elections. It was brutally cold, so Sydney got sick and completely does not remember the hearing Kid Rock at the Romney rally they attended ...but she does remember the young man who sat down with her to make sure she was okay when she was too sick to walk anymore. Caleb doesn't remember this but he does remember arguing over whether or not Wendy's Frosty's are ice cream, as well as Sydney talking about swimming. Caleb's brother Sam, who was also on the trip, commented that he remembers her being 'very home schooled'. It was a good trip; there was a lot of door-knocking, a lot of phone calls made, and a whole lot of Oreos eaten, but when it ended no one thought so many lifelong friendships had been formed.
Sydney's junior year of college she was going on a summer study abroad trip to Italy, however, due to British Airways having technical issues with their computer system, her connecting flight to Milan was cancelled. Suddenly, she found herself stuck in London with no hotel, no suitcase, and no plan. Meanwhile, Caleb was working his way through his junior year at Maine Maritime Academy and was waiting for his summer training cruise to begin. He saw a post of her holding her flight tickets, and so, curious he reached out. The conversation started with a simple “Where are you off to now?” and not even a lack of cell phone service stopped them from staying in contact over the next year. Over a year later in December of 2017, Caleb decided to come down to Rhode Island to meet up with Sydney. This was the first time they were going to see each other in person since 2012, and the plan was for Sydney to pick him up at the Providence Train station and then meet the rest of her family at Santas Village to spend the day. While the two had a strong friendship, and spent lots of time talking to each other on the phone and through texting. Sydney was still very nervous. "What even is this?" she wondered, "We aren't courting, we are just friends, so why do I feel so flustered?" She parked at the mall across the street and started walking across the grass to the station. When she was almost at the doors she saw Caleb walk out. Suddenly, she felt very frazzled and so not knowing how to greet him she pretended she didn't see him and kept walking straight forwards! Caleb saw her though and called out "Hey, Sydney!" Sydney turned around. "Oh hey," she greeted, "Haha I didn't see you there." Fortunately, despite this awkward start, the rest of the day went quite well and both were eager to set up another day to get together.
Sydney: In spring of 2018 while visiting Brentton Point, Sydney sat talking to God saying "God, I'm not sure what to do, either this friendship needs to move forwards into something else or we need to take a step back". Caleb: At the same time Caleb was sitting next to the prettiest girl he’d ever seen and he knew that he needed to ask her if she wanted to move forwards into a relationship beyond that of just friends. He sat taking short breaths with sweating palms just trying to think of what to say and how to say it. Just a few weeks prior, this beautiful young woman had graduated from college and now had plans for returning to school to earn her masters. “Should I ask her now or should I wait until she completes her schooling? I can wait, she’s the girl I’m going to marry, I know that for sure. But should I wait for her to finish the next two years or do I ask her now? What do I do?” Sydney: Right as she finished praying this Caleb turned to her... Caleb: Looking at her watching waves hit the rocks, he knew what he needed to do. “Hey... um, Sydney. I have something I want to ask you.” She turned to look at him. Taking a deep breath he continued “Sydney, do you want to see if we’re meant for something more than friendship? Like the C.S. Lewis quote, do you think we are supposed to be looking at each other standing face to face, instead of just walking side by side? ...What I mean is, will you enter into a courtship with me to see if are meant to be married?” Sydney: Sydney was so surprised by this immediate answer to her prayer that she just said "Sure". The next couple weeks were filled with the two talking with their parents to decide what they wanted this courtship to look like, what their guidelines would be, and how they would encourage one another to grow closer to God.
From the moment Caleb stepped off the train in Providence and saw Sydney (dressed in her paddington bear coat, black turtleneck, jeans, and tall boots) walking across the grass; he knew he was going to marry her. And visiting the Borges family in Eagles Mere, PA, he knew the exact place he was going to ask her. All he had to do was talk to her father and pick out a ring to set it all into motion. So, on January 21st, 2019, while visiting Sydney in Rhode Island, Caleb asked Mr. Borges if they could get breakfast and talk. (He thought he was very inconspicuous, but a few months later Caleb learned that Sydney knew exactly what was going on that day.) They drove down the road to a small cafe, Caleb ordered a coffee (black) and Mr. Borges ordered a sesame seed bagel. After a few agonizing minutes of small talk (by agonizing Caleb means that he was ready to burst out saying “Can I marry your daughter?”) that seemed like hours, Mr. Borges finished his breakfast and Caleb told him that there was another reason he wanted to have breakfast with him. He told him that he loved his daughter Sydney (the first time Caleb had ever told someone that he loved her) and that he wanted his blessing and permission to marry her. To his relief, Mr. Borges said yes! Having received the blessing, Caleb set out to pick the ring. It took him four months before he finally found the right one. As May approached, Sydney and Caleb made plans to road trip back to RI from Athens, GA where Sydney was in school. It was a long trip, but they made plans to stop and visit different places and people on their trek back north. Knowing that Eagles Mere was going to be one of those stops, Caleb called Mrs. Borges. He needed help to be able to to set up and decorate the place he had picked out to ask the biggest question of his life.
After less than a year of courting, Caleb knew he wanted to marry Sydney. (Well actually, he claims that he knew it from the moment he stepped off the train and saw her in Providence), but Sydney had just started her first year of grad school so he wasn't sure when would be the right time to ask her. In the fall, while walking around Athens, Caleb mentioned that he was thinking about asking her 'soon' but then said no more about it until May 7th, 2019, so Sydney was just left pondering what 'soon' meant. (Sidenote: if Caleb says he's going to be somewhere 'soon' anticipate him arriving approximately eight months from then.) In May of 2019, after Sydney finished her first year of grad school, Caleb took a few days off of work to help her drive back to Rhode Island. On the way, they planned to stop in Eagles Mere. They got there pretty late at night and since there was no food at either house they went to The Barn to get dinner While they sat there eating dinner Sydney had no idea that elsewhere in EM the Liebert’s were busy covering the footbridge in twinkle lights and candles. After dinner, despite the cold and dark Caleb suggested they go for a walk around the lake. They parked at the Village Green and walked down to Edgemere. Unfortunately, because it had been raining all day, the Laurel Path was soaked so Caleb had to carry Sydney through the muddy parts where her plastic Jack Rogers couldn’t get traction. Finally, after walking a ways down the path he asked her to close her eyes. Sydney could tell that they had walked out onto the footbridge when she heard him say, “Okay, you can open your eyes now”. When she opened her eyes she saw that the footbridge had been covered in twinkle lights and lined with candles, she turned around and he was down on one knee. Sydney says "I honestly don’t remember much after that, in fact, afterwards, I had to ask Caleb 'Did I remember to say yes?' "