Jill and Jason

How We Met

I was in my freshman year of college and my birthday fell on a Tuesday. My roommate, Kayla, and I wanted to celebrate but had no plans. A cute boy down the hall (Jason) was looking for a reason to crack open the Franzia he had laying around. So, he invited us and a few other floor mates over. At this point, it was October, and we had seen each other in the dorms, but never really spoke. We got to know each other over cheap boxed wine. We bonded over our love of dogs, Jewish heritage, and weirdly enough, our thoughts about the existence of aliens. I distinctly remember going back to my room that night and sharing with Kayla that I totally had a huge crush on Jason.

Proposal Ideas Maui, Hawaii

Engagement Proposal Ideas in Maui, Hawaii

Over the next few weeks, we began to see each other. Eventually, it was time for our school’s 8-week winter break. I was nervous the excitement would fade over such a long period of time as we never declared ourselves as “in a relationship.” However, Jason promised he’d come, visit me in my home state of New York. In keeping with his promise, Jason and I met up on January 16, 2012, in Manhattan. As a native Pennsylvanian, he wanted to go to the top of the Empire State Building. Looking back, Jason said he had no idea it would cost a few hundred dollars to do so, but he was too embarrassed to back out of it. And so, we went on a very expensive first date (given that we were broke college kids). At the top of the empire state building, Jason asked me to be his girlfriend. We have been inseparable ever since!

Jill's Proposal in Maui, Hawaii

Wedding Proposal Ideas in Maui, Hawaii

Jill and Jason's Engagement in Maui, Hawaii

How He Asked

Jason and I totally have the travel bug! This year, we decided to go to Hawaii to celebrate the end of my first year as a professional School Counselor. In the months leading up to our trip, I kept dropping some (not so subtle) hints to Jason about how my dream would be to have an “engagamoon” in Maui. Jason said he would try his best to get a ring in time, but he was in busy season at work (he’s a CPA). A few days before our trip, Jason sat me down and broke the news that he could not get the ring in time for the trip. He said he wanted to let me know now so that I wasn’t on edge all trip waiting for a proposal. I was bummed, but still so excited to see Hawaii.

Fast forward a few days, and we are about to check into the Ritz Carlton Kapalua. Jason tells me he is going to call and ask for a room upgrade and pretend we are getting engaged. I was so annoyed because this was a “sore subject.” So right in front of me, Jason called the Ritz and said that he was proposing to me that night. At this point, I still thought Jason was just playing the front desk people so we could secure that ocean front view.

Once we got to the Ritz, we started to get ready for our fancy dinner that night. Since we were all dolled up, Jason said he wanted to go take a picture on the beach at sunset. When we sat down on the beach, Jason said he had a gift for me. He pulled out a photo album. (For background information- I had made Jason a photo album this year for our 6 year anniversary. Unfortunately, our crazy puppy ate it.) He said he made me an album since he knew how upset I was about the album baby Chloe destroyed. Jason’s album was equipped with a poem throughout narrating our 6-year romance.

Towards the end, the poem said: “so Jill, my love” and when I hastily went to the next page, I unknowingly skipped the page that said “will you marry me?” and went right to the blooper reel. So I am looking down at a picture of me cross-eyed while I look over and see Jason on one knee! Jason exclaimed, “No, go back a page!” I quickly flipped back and saw an adorable picture of our puppy with the ring and the caption “will you marry me?”

I think it took me 20 minutes to even say yes! I was in such shock. I just kept yelling “no way! woah! no way.” We were hugging and kissing when a man came over. I had noticed him in the corner of my eye taking pictures of the sunset (or so I thought). He introduced himself as our photographer. He had been capturing the proposal the whole time! And so, we were able to take beautiful pictures on the beach with a picturesque Maui sunset, a ring on my finger, and giddy grins on both of our faces. We are so excited to be getting Maui’d!

Special Thanks

Rafael
Photographer