Loni and Jessica

Where to Propose in North fork, Long Island

How We Met

Jess and I came into each other’s lives at the perfect time. We are both special education teachers and she worked for a school district that contracted the company I worked for. Our work environment was intense. We both had students with severe disabilities, who actually didn’t get along AT ALL. Even though we had to keep our students apart, it didn’t stop us from getting close. We became fast friends by bonding over Thai food, our love for traveling, and binge-watching TV shows.

Marriage Proposal Ideas in North fork, Long Island

Engagement Proposal Ideas in North fork, Long Island

How She Asked

Jess and I were together a year and a half when I proposed. We had planned a trip to Provincetown, MA, and we would be traveling through the North Fork to take a ferry north. Our first trip together was to the North Fork on Long Island, and we had since visited there often. We took our first picture together on a beach out there that was off the beaten path, so I decided to recreate that moment.

We are both very close with our families, so I knew we’d want them involved. Jess has a twin sister, Ally, who is also her best friend, and my older sister, Shira, is mine. I decided to enlist them to capture the proposal on film. The plan was for Ally and Shira to hide in the dunes at the beach and wait for us to arrive. They took their job very seriously, and dressed “incognito,” complete with trucker hats, sunglasses, and fanny packs.

The proposal went off without a hitch. I put my cell phone on a tripod and stuck it in the sand to take a selfie, and as Jess was adjusting the angle, I took out the ring. When she turned around, I reminded her of all the amazing times we’d had together, and how much I was looking forward to spending the rest of our lives making memories together. When I showed her the ring, she said yes without hesitation! While we celebrated together, Ally and Shira snuck off to join the rest of our families at one of our favorite restaurants.

Once in the car, Jess started to make phone calls to tell her family the good news. After speaking to her mom and sister, both of whom were fabulous actresses, we arrived at the restaurant. She was actually on the phone with her dad when we rounded the corner and saw everyone waiting for us, all decked out in coordinating “Jess & Loni” rainbow T-shirts that even I hadn’t known about! We spent the rest of the day drinking, eating, and celebrating our news before Jess and I headed off for a week-long vacation. A few weeks later, Jess proposed right back and of course, I said yes. We’ll be married next Memorial Day weekend, and it’ll be the best day of our lives!