How On Earth Did These Two Meet?

It was a beautiful, sunny winter day on December 29, 2022, and Ashton and Tony were about to meet for the first time! They both signed up on eHarmony just weeks before – without high expectations. Both of them were very cautious about online dating and somewhat doubtful of the process. They had no mutual friends or connections. Nonetheless, both of them were believing Christians who had prayed to the Lord for a spouse for many years – and each of them were willing to give it a shot. They also had become quite intrigued by each others' online profiles!

The First Date

After exchanging a few online messages, Tony asked Ashton for a first date. She accepted, and they agreed to meet at the Mountainside Café in Falls Village, CT for a casual lunch. The restaurant was conveniently located at the midpoint for each of them on Route 7 – between Lenox, MA (Ashton’s home) and Bridgewater, CT (Tony’s home).

The first date was a pleasant surprise in light of the initial nervousness. There was an instant connection. They felt like they were two of a kind, and so comfortable with one other! They had many laughs together and shared many of their life stories with one another. There was such chemistry! They discovered so many commonalities - their faith in the Lord, the fact they were both homeschooled, both their fathers were business owners, both their moms were into health and nutrition, and they both loved their jobs. And it was amazing how fast three hours flew by!

Shortly after the first date, Tony began to feel that it wasn’t the right time to start a relationship with Ashton, despite his strong interest in her. This was mostly due to Tony's work demands between January and April 15th as a tax manager of a local CPA firm. This came as a disappointment to Ashton, and it wasn't fun for Tony to communicate this to her. They respectfully agreed to talk again after tax season was over. But at the time, it appeared that the beginning of something great had hit a dead end…

The Second First Date

The following summer, Ashton texted Tony to check in with him. He had just finished a business valuation certification for his job which was a grueling and time-consuming process. Her text came as a total surprise to Tony – who had long assumed she had been swept off her feet during tax season by someone else and that he had missed out big. And it could not have come at a better time.

Tony asked her out for dinner – this time closer to her home in Great Barrington, at the restaurant Number Ten. Both Tony and Ashton had some doubts and feelings of nervousness about meeting again. As Tony made the long drive up north on Route 7 to Great Barrington in torrential rains, he wondered, “Why am I driving this far out of the way on a Sunday night?”

When they both arrived at the restaurant, Tony held the door open for Ashton, who came in out of the rain a minute after he did and folded away her umbrella. They exchanged greetings and she laughed. Then he laughed. Then she laughed! In that moment, he knew exactly why he had driven up there: For all the fun and laughs they shared the first time! And the rest of the evening was full of laughter and learning about one another all over again. At the end of the evening (another 3 hour meal) and a very awkward goodbye, each of them felt a ‘tug’ of wanting to see each another again.

More Dates…

They connected again for another date in New Milford, CT a couple weeks later, closer to Tony’s home. In the following weeks the spark of interest quickly grew into a romance! They began dating regularly, while feeling unusually comfortable and joyful around each other. The more they learned about each other, the more the ‘magic’ grew. They had several fun dates and never without lots of laughter over everything and nothing at all. Their dates included a few concerts at Tanglewood in Lenox, various hikes, dinner with each other’s closest friends, and axe throwing.

About three months into their relationship, Tony started to seriously contemplate whether Ashton was the delightful woman he had prayed for (and waited for) all those years. She was sweet, kind, and encouraging of him in all his endeavors – professionally and personally. And for Ashton, Tony was such a steady source of love, security, and comfort for her, and she was beginning to wonder the same thing.

It Gets More Serious

As the Fall months ended, the couple witnessed a crisis. On the Saturday following Thanksgiving, a fire broke out in Ashton’s apartment while they were inside. Both of them escaped, while the flames destroyed her apartment and all of her belongings. In that moment of panic and helplessness, the couple learned to depend on each other in a much deeper way not previously known in their lighthearted dates. The event confirmed for Tony his feelings that he would step in to take care of Ashton no matter how bad things were – and it affirmed for Ashton reliance on Tony for comfort and strength in a very real way. From that point on, the couple's admiration grew for each other, and they became much closer after that.

By New Years, and through much prayer, Tony had conviction that Ashton was the one the Lord had chosen for him. Ashton had a similar conviction - and she secretly hoped that Tony would propose marriage in the near future.

The Proposal

On February 3, 2024, Tony proposed marriage to Ashton. He woke up that on that Saturday morning with her engagement ring in hand, and a plan. He enlisted the help of Ashton’s friend Heather to ask Ashton for a walk at Tanglewood that morning, the site of a memorable date early in their relatioship. Ashton had no idea that Tony was coming to visit that early in the day, and it was to be a total surprise. After some coercing, Ashton agreed to go on the walk with Heather.

Meanwhile, Tony was racing up Route 7 from Connecticut to Lenox. Before Ashton arrived, Tony and Heather set up a table with champagne and cheese and crackers at the exact spot where they had their picnic on the date. Ashton arrived, and they walked right past the table, without her knowing anything. She remarked to Heather about how ridiculous it was for someone to set up a picnic in February! She took a picture of the table to show Tony later.

Tony, frantically texting Heather from a hiding place got a text that now was his moment..... He began walking towards them from behind, catching up to them. Ashton turned around, and was surprised to see him. But when she saw Tony standing there, and as he led her closer to the nearby table with champage, she got teary-eyed with joy as she realized what was about to happen. He knelt down on one knee and asked her for her hand in marriage.

Needless to say, Ashton said yes!!

The Mount, Edith Wharton's Home

Tanglewood