Get your tissues ready because we’ve got another contender for the best Bridal musings proposal ever!

Without giving anything away, we can’t help but gush over how adorable Jennifer & Jack’s engagement story is. But we’ll get you ready with a movie-like introduction. Jack planned to propose to Jennifer while visiting family in South Carolina. As they always do, family surprises got in the way. After several failed attempts, the couple decided to fly their separate ways.

The rest of their proposal story is up to them, but we think it was cinematic gold. Jack and Jennifer jetted to the cliffs at Capri in true dramatic style for their breathtaking elopement. Rotten Tomatoes gives this wedding 100% because of its cinematic views along the Amalfi coast and the obligatory boat trip.

The Proposal

Jack planned to propose after five years of dating. However, with his youngest brother’s engagement celebration planned that weekend and other events, he could not find a suitable time. He planned to propose on Sunday morning before we headed to the airport. However, his middle and younger brothers were leaving early to celebrate their anniversary. All of this would set the scene for a spectacular proposal.

He was thinking about the best way to see me next. He planned how to do it on our flight from Columbia, SC, to Charlotte, NC. He lived in New York then, and I was in California. I was on a long layover as his plane left Charlotte shortly after our arrival. I told him I would probably spend some time at the seafood restaurant during my layover. I said goodbye to him, watched him get on his plane, and then went to the restaurant.

Around an hour later, I felt someone tap my shoulder. It was him! I didn’t know what to expect. He explained that he would propose on Thanksgiving, but things didn’t go as planned. He also said he couldn’t wait anymore and realized this while sitting in his plane. He grabbed his bag, rushed to the front of the aircraft, and asked for a ride. The jetway was already gone. It was like something out of a movie! Surprising a girlfriend after five years is difficult, but that proposal was a complete shock.

We both changed our flight times to the same time the night after he proposed. We spent the following few hours drinking champagne and hanging out. I also bought new heavy coats for New York in preparation!

Dress & Attire

When it comes to wedding planning, a bride is supposed to list her three top priorities. For me, that was the dress. I was looking for something timeless, classical, elegant, and, surprisingly, it came to me quickly. Hayden Olivia Bridal, in Charlotte, NC, was my third stop. The dress I selected was the very first one I tried on. The dress was part of a trunk show that would leave in 24 hours. I had to decide quickly. After I left the shop, I could not stop thinking about this item. It’s safe to say that I made the right choice. The dress I wore was “Candice,” a design by Anne Barge. My husband wore a classic black tuxedo by¬†Brooks Brothers.

Favorite moments

We exchanged vows on a cliff with a view of the Mediterranean Sea at the Hotel Caesar Augustus. The hotel provided a string quartet and a delicious array of appetizers and champagne for us to drink as soon as our wedding ceremony began. It was a wonderful experience.

We will never forget walking around Capri in Italy and feeling like film stars for a day. Locals congratulated us everywhere we went. The next thing on our agenda was a boat tour around the island. This was my favorite part of our day. We had already taken the most important photos and could relax and view the island from the boat. We enjoyed a romantic dinner at the hotel in a cave-like setting. We will never forget this day.


We spent two more days at the Hotel Caesar Augustus, where we were married, before we left for six days in Florence. We stayed in NH Collection Firenze Porta Rossa and took city tours. We also enjoyed wine tastings in Tuscany. It is known as one of the most romantic cities on earth, and I highly recommend it for your honeymoon.

Couples Advice

Before planning my wedding, I chose the three most important things for me and dealt with them first. It was the venue, the dress, and the photos that were most important to me. You should book them early, even if they aren’t your top three. Securing your hair and make-up stylists in advance is probably a good idea. I ordered my bouquet at the last minute. As important as the arrangement was, I sent the florist a list of about four or five different colors and styles I liked. I left it to them to surprise. It was beautiful! It was beautiful!

If you are considering an elopement, you should contact our photographer, Rochelle Cheever. She is a specialist in small weddings and elopements. She took some of the most beautiful photos on our wedding day. She also helped me to plan my day so that I could get the best shots. She was very knowledgeable about Capri and Italy and guided us to the best places to visit after the ceremony. She is incredible!

If you are thinking about getting married on Capri in Italy, stop and call Hotel Caesar Augustus. They were accommodating. The staff will handle all your needs, from an English-speaking officiant to flowers and food for the dinner and ceremony, appetizers, drinks, and cake to pressing the gown for the big day. The hotel also sits on a cliff with a view of the Mediterranean Sea. They have several beautiful spots for weddings.