Caitlin & Christopher

November 8, 2025 • Waitsfield, VT
240 Days To Go!

Caitlin & Christopher

November 8, 2025 • Waitsfield, VT
240 Days To Go!

Our Story

Our Story

Told by Chris


All great relationships start with honesty. Ours started with trickery!


Our story begins at the gym on Christmas Eve in 2021, masked up amidst the pandemic. I was leaving the gym when I passed a cute, curly haired brunette in the parking lot…she was scurrying into class late. After some sleuthing I found out Caitlin Schlesinger works out most mornings at 5:15am, and she was single. I did what every logical person who hates the morning and is currently waking up at 8:00am to work from home would do…I started waking up at 4:30am and going to the gym, trick #1. I had only seen half her face, nose and mouth covered with a blue medical mask…so yea, she had a nice butt.


After a few weeks of dragging myself out of bed with the hope of seeing Caitlin at the gym, I built up the courage to ask Caitlin to grab a coffee after a 5:15am class. A benefit of it being so early in the morning, was that we both needed coffee to function. Even with the coffee, I was coming home and taking a nap until work. The first time we ‘hung out’ after work was when I asked Caitlin to go for a run after work along the Charles a few days later. This was also the first time I saw Caitlins face, like I said…good butt. I hate to run, so this was trick #2. Later that week we went on our first date to Olivia’s Bistro in Newton, MA. Caitlin considers this as the day we started dating. I disagree and think it is April 9, 2022. That was also the date when I stopped waking up and going to the gym…trick, complete.


Parents were met. Holidays were shared. We vacationed and traveled. We got Bogey, and Banjo hated it. We moved in together. We fell in love with Burke VT, so We bought land. We got engaged. And now the best is to come!