Angela and Mitchell

Where to Propose in Portofino, Italy

How We Met

Angela: Mitchell and I met a little over 2 years ago when we were living in the same apartment building in Chicago. I was lying out by the pool when this boy came up to me with what I thought to be rotten teeth and started to chat. He told me he had just moved into the building (which I would later find out was a total lie), and that he would love for us to be apartment friends. I eventually gave him my number, mostly just so he would go away.

Over the next month, he texted and would drop by my apartment from time to time. I wasn’t really interested. I did discover, however, he has nice teeth, he just had food all over them the first time he came up to me, which his friends let him know immediately after, and he was mortified.

I was going to Australia to work for several months, and in one last attempt, this persistent man-made a dinner reservation at a nice restaurant and insisted we go on a proper date. I caved. It was just one dinner before I would be leaving the continent for a while.

We ended up having a blast. He’s a very handsome man when he doesn’t have food all over his teeth, and even when he does really. We clicked on so many levels I did not expect. While I was gone, we kept in touch. And when I got back, he picked me up from the airport with wine and flowers. The rest is history. We were inseparable after that and even ended up moving across the country together. I can’t believe I almost missed out on the most selfless, caring, hilarious, fun, man and best cook I’ve ever met!

Mitchell: One day in June a few years ago, several of my college friends were in town for a wedding. The day of the wedding, I hosted a brunch on the deck of my pool where we could gather and socialize prior to the evening festivities. Towards the end of the meal, one of my friends looked to the pool and said there was a beautiful girl in a black bikini. I looked in her direction and saw Angela stretching to put her hair up. Time slowed down as her perfect figure was silhouetted by the sun, my jaw dropped and I immediately found myself speechless.

As the only single man there, all my guests urged me to go talk to her. I couldn’t. I’ve never been the type of person to just talk to someone new, and most importantly I knew they would all be watching and I would be humiliated when she inevitably rejected me. Eventually, the conversation moved topics, but I couldn’t stop staring her way. I knew I had to just somehow find a reason to talk to her. When it was time to leave and all of my friends were distracted with packing up, I saw my opportunity.

I approached and introduced myself, the first thing I said was simply “Hi – I’m Mitchell.” I asked if she had lived in the building for a long time, and told her I just moved in (which was definitely a lie) and didn’t know anyone at the building. Throughout the whole conversation I said so many things that I remember thinking immediately afterward, Why would you say that? The worst was probably telling her I liked to cook and that maybe we could be apartment friends. Somehow I ended up asking for her number and was shocked when she gave it to me, even though I still suspected it was fake. By then my friends had noticed, and I walked back to them with a distinct swagger. When I rejoined the group I elbowed one of my guy friends and asked him how cool that was. He looked at me and responded, “Dude you have stuff all over your teeth.”

Engagement Proposal Ideas in Portofino, Italy

How They Asked

Angela: Mitchell and I love to travel, and we had our biggest trip yet coming up, 2 and a half weeks in some of the most beautiful spots in northern Italy. I knew this would be the trip of a lifetime but had no idea on this level! Our second stop was the beautiful, small coastal town of Portofino. We spent the first couple of days walking around, eating delicious food, drinking delicious wine, and taking in the views. He had a nice dinner reservation planned for us the next evening and avidly reminded me that I have to be ready on time because they won’t hold the table, and that this will be the best photo op night. I also noticed him frequently checking the weather. It’s not uncommon for him to plan nice dates, so it wasn’t a giveaway. He told me the location was about an hour away, and what time the car would pick us up, so I could be ready. The hotel called up to tell us our car was downstairs, so we headed down. There was no car, there was a photographer waiting downstairs, and Mitchell said he lied, and actually wanted to surprise me with a photoshoot! Dinner would actually be close by in town and would be much later after the shoot. I was so excited.

Proposal Ideas Portofino, Italy

As we walked through the alleyways, streets, and up a mountain by the shore, Gabri, our photographer, snapped all kinds of photos of us, and he was so much fun to work with. Eventually, he told us we would end the shoot in this spot by the docks with one of the best views. After taking these photos, he was just like okay, we’re finished. We were about to head back when Gabri suddenly said that it would be awesome to get some shots on one of these yachts. He said it was a crazy and hilarious idea, but he was going to ask a driver sitting there alone if we could take pictures on it. They went back and forth speaking in Italian for a while. The man on the boat agreed. We took a few shots, then Gabri said he was going to ask the man if we could go out for a quick ride. Once again, they went back and forth, and the man agreed. We started sailing away, and at that point, the gig was up. I asked if Mitchell planned all this, and he did! He had organized the whole thing and chartered the boat for us for the evening!

Angela and Mitchell's Engagement in Portofino, Italy

We went out to the front, the driver turned it around and said he thought this was the best view of Portofino. Gabri went to snap more photos of us and told Mitchell this pose was his call. At that point I know it’s happening, but I can’t believe it’s happening! He is down on one knee with the ring box telling me how much I have changed his life for the better and ends up cutting his speech short because he couldn’t remember the rest. How could he with me jumping around squealing? Luckily, my resourceful man wrapped the ring with dental floss and glued it to the bottom of the box. His thinking was protection from potential waves knocking it from his hands, but it definitely helped when I tackled him! The rest of the night was magic, cruising around the Italian coastline with my fiancé drinking champagne, and an amazing dinner when we got back to town. As if this weren’t enough, he booked an engagement shoot session with the same photographer for us later in the trip when we got to the Dolomites. This man makes my life a DREAM.

Marriage Proposal Ideas in Portofino, Italy

Angela's Proposal in Portofino, Italy

Mitchell: A few hours after getting Angela’s number I texted her and [unsurprisingly] didn’t hear back for 24 hours…so I thought that was that. Eventually, she did text me back and we scheduled a date to get a casual drink. I was pretty nervous and ended up drinking a bit too much, and it didn’t go great. Over the next couple of weeks, I would see her here and there, but I could tell she wasn’t really interested and the intervals between the time we would spend together began to increase. I had all but given up when I saw on social media that she had accepted a position in Australia, literally the other side of the world, and would be leaving in a few weeks. I decided to try a hail mary and made a reservation at an extremely nice restaurant I knew she would have a hard time saying no to. We went, and it was the best date of my life. Every day from then until she left for Australia we spent together, and I was devastated when she was gone. I was so nervous about what would happen over the course of the next several months, how would I be able to maintain her interest with so much distance between us?

Somehow the time apart passed, and we stayed in touch – regularly video chatting a few times a week. I began to fall for her, and as time passed and I missed her more and more I realized that I needed to spend the rest of my life with this girl. Over the course of our two-hour-long video calls, she became my best friend, and nothing else in my life mattered. It was all just going through the motions until the next time we could talk. Eventually, she came home, and I picked her up from the airport, stopping beforehand at a convenience store to buy a coffee mug and pour some red wine in it so she could take the edge off the flight on the ride back to the apartment. We haven’t been apart since.

About a year into our relationship, in November, I took her ring shopping. Eventually, she tried this particular diamond, and I knew immediately that was the one. The next day, I called the jeweler and put a deposit down – after seeing her light up from that ring I wasn’t letting it go. We had been planning a trip to Italy for the following July, and I knew that would be the ideal time. It was a long time to keep a secret, but I wanted the proposal to be perfect.

I wanted the moment to be intimate. More importantly, I wanted it to make her feel like a princess. Ultimately, I came up with the idea to propose on a yacht in Portofino, a luxurious village off of Italy’s north-west coast. In December, I began talking to charter companies, and by February I had confirmed a boat as well as a photographer. When the day came she was expecting to go to dinner, so she was extremely surprised when a photographer met us in the lobby of our hotel. She probably started to grow suspicious, but she had been asking to do couple photos for a while at that point, so it wasn’t a complete giveaway. We took photos around the city, and I eventually surprised her with the yacht. Once we got into position, I got down on one knee, and all I can remember was that I was terrified. I can’t believe how lucky I have been since the moment I met her. I can’t believe she gave me her number in the first place, I can’t believe that my persistence wore her down and she agreed to go on a real date with me. I can’t believe we stayed in touch after months apart. Most of all, I can’t believe she said yes.

Special Thanks

AMM Charter
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