“It Was The Easiest ‘Yes’ Of My Life!”: Danielle & Anna’s Proposal Story

by Taylor Team

How We Met

We met about five years ago in May of 2015. Danielle was doing her study abroad in Rome, Italy, and we would all go out at night with mutual friends. We officially started dating later that year, and now, after a proposal, and then another, we’re engaged!

ANNA: When I first met Danielle, we were in Rome. It was 5pm – she was eating pizza with knife and fork and didn’t know what a Spritz was! A group of our friends wanted to go to the nearby Rocca Massima to fly down the mountain on a rope. Danielle was so excited; she was like “I have to come! My family is from there, so I have to!”

Little did I know that that was the beginning of our friendship, which evolved into love. Since then, Danielle has become my rock. She’s always smiling, no matter what. Whenever I start to have anxiety, she is always there to give me comfort and calm me down. She is my number one fan. She taught me not to be afraid of showing my feelings. I feel so, so lucky to have her next to me and call her my wife now!

DANIELLE: I just knew that Anna was the most special person I had ever met. There was no way I could let that pass by! She is my rock and forever soulmate.

The First Proposal:

DANIELLE: A couple of days before Anna’s proposal, we flew into Milan and drove to the region of Trentino to meet up with her entire family. We had just finished a morning hike in the Dolomiti mountain range when it began to rain. Rather than head back to the hotel with the others, Anna convinced me to go for a drive in hopes of finding a place to take some cool drone footage. Upon setting up camp, she pulled out her ukulele and started to play our song, “Home” by Edward Sharpe… all while personalising the lyrics to tell our love story!

After finishing the song, she pulled out a little wooden box. Expecting to find a diamond in there, you can imagine my face when I found an orange-flavored Ring Pop instead! (Anna and I always joked about her getting me a Ring Pop instead of an actual ring in a proposal so it was kind of hilarious!) What was even better was what happened next. She opened a little black box with the most precious ring and asked me those five little words – “Amore mio, mi vuoi sposare?” [‘My love, will you marry me?’] With tears in both of our eyes, I can say that it was the easiest “yes” I’ve said in my entire life.

The Second Proposal

DANIELLE: Just two short months later, I decided that it was my time to pop the question! Anna had just landed in Miami the day before, so she was still a bit jet-lagged. I convinced her that we should stop by this park overlooking the Miami skyline before dinner, and off we went! Little did she know that I had my sister set up a romantic picnic with our favourite wine, fresh flowers, candles and a variety of the most delicious mini-cakes! Upon entering the park, we saw a bunch of well-dressed people doing photoshoots, so when we “stumbled” along with the picnic it hadn’t phased Anna yet.

I then whispered to her, “Hey – should we go crash that picnic?” She immediately looked at me as if I was crazy! At that moment, I got down on one knee and asked her to spend the rest of our lives together.

The best part was that she had NO idea! She immediately said yes, and it was by far one of the best moments of my life! We spent the rest of the evening enjoying the sunset, sipping wine and eating way too much cake – it was perfect.

How It Happened

ANNA: I was really taken by surprise with the proposal. I knew that Danielle was going to do it, but I did not know when or how.

I was visiting her in Miami, (one of the last times before I moved there). Still feeling a bit jetlagged, and after spending the morning and lunch with our nieces and family, we went back home to take a nap. She told me that we were meeting with a friend of ours for dinner, and before that, going to a park to do some drone flying at sunset.

I should have noticed that something was different when she didn’t nap that afternoon – Danielle is a big napper! She kept waking me up, and I was kind of upset with her. For once, I was the one who wanted to nap, but she kept waking me up to go to see a sunset.

Little did I know that, when we got to the park, she was like: “Let’s go over there and see the sunset!” There was a picnic set up, and a very well dressed couple nearby, and, again, she was like: “Let’s go and check it out!” She dragged me over to the picnic, and I tried to stop her. It looked like it was clearly theirs, and I couldn’t understand why she wanted to crash the picnic! As I turned towards her, she got down on one knee and asked the big question – “Will you marry me?”

I was so speechless and surprised because I really didn’t see it coming! As we got closer to the picnic, I noticed that there were all of our Polaroid pictures spread out, as well as our favourite wine and cake. All of the details of the picnic set up. From our pics to our favourite wine, cakes, lights and candles. It was all so beautiful and expressed all the love we have.

Where We Are Now

Anna and I have been living together in our new home in Miami, Florida for the past three months. We are loving it! Of course, we miss the Italian lifestyle, but we’re keeping ourselves busy with work and some local travel. We decided to elope last weekend in Fort Myers with just our family present. Although it was not our first option, it turned out to be so special and beautiful. We still have our big wedding celebration planned in Italy for the upcoming year. We hope borders will open and it will be safe to celebrate all together soon! Either way, we are so thrilled to finally be together and we will never take that for granted!


Check out Danielle and Anna on Instagram here!

To read more stories in our proposal series, check out our Matters of the Heart section here!

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