Part 1: The Beginning of Our Timeshare Story
It started about 15 years ago with what should have been a simple errand: taking the kids to the sporting goods store for winter jackets. While they admired the live fish in the tank, we wandered down a winding staircase to the lower level. That’s when we saw her—a woman standing at a podium beside a sign that read, “Enter for a Chance to Win a Free Vacation.”
If you’re a parent, you know how magical those words sound. A free vacation? Yes, please. We filled out the form, never thinking we’d hear from them again.
But a few days later, the phone rang. To our surprise, we had actually won. After confirming it was legitimate, we packed up the kids and headed to New Hampshire for a free weekend away—Whale’s Tales, Clark’s Trading Post, waterfalls, train rides, and of course, the hotel’s indoor pool. The only catch was that we had to attend a timeshare presentation. Still, they promised us a $100 gift card for our time, which sounded like a pretty fair trade.
When we arrived, we were told the kids could sit with us briefly, then play in a separate “kids’ room.” We weren’t thrilled about leaving them with strangers, but we were assured we could check on them at any time. Reluctantly, we agreed.
We were ushered into what felt like cubicle city—a noisy, partitioned conference room buzzing with chatter, music, and sales chatter. It was overstimulating to say the least.
That’s when we met our salesman—let’s call him John. He was warm and friendly, offering us coffee and small talk before diving into the pitch. He painted a picture of carefree vacations, explaining how their points system was far superior to old-fashioned “weeks.” With points, we’d never have to worry about hotel rooms again. We’d have access to countless resorts, plus the ability to exchange points for even more destinations.
It sounded almost too good to be true.
Then he slid a sheet of numbers across the table. My heart sank. I told him that with possible budget cuts at work, we couldn’t afford anything risky. That’s when he asked about my job. I explained I was a federal employee and that my husband was in the military.
Suddenly, the mood shifted. John leaned in, thanked my husband profusely for his service, and hurried to get his manager. The manager arrived, shook my husband’s hand, echoed the gratitude, and then unveiled the hook: “For today only, we can give you an incredible deal—our way of saying thank you to your family.”
The details are fuzzy now, but at the time it felt doable. After nearly four exhausting hours, we signed the paperwork, collected our $100 gift card, and took the kids out for a celebratory lunch.
We walked away believing we had made the best decision for our family. What we didn’t know was how much that single signature would come to cost us.
