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How I Met The One Finale: The Proposal

Every woman in the world dreams about a Prince Charming-like wedding proposal similar to what they see in Walt Disney fairy tales and Hollywood romcoms.

And men, often go to great lengths to fulfill that dream for women. That is, pulling off a magical (albeit pricey) proposal hoping to sweep their girl’s feet off the ground and get that elusive “Yes”.

In the course of history, we’ve seen guys do the unusual and things you just won’t forget: Men surprising their girlfriends with giant “Will You Marry Me?” billboards. Guys putting up an elaborate, candle-lit dinner date at the garden with petals of roses scattered all over the floor. Dudes kneeling in front of the crowd during a live concert (and borrowing the microphone of the band’s vocalist) to ask the billion dollar question:

“Will You Marry Me?”

All that sounds fun, fiction and games, until it is YOUR turn to propose marriage.

And that was my exact problem back in 2016, when I was about to propose to my girlfriend, Joan.

See, the story of Joan and I was a long one with many surprises and ups and downs in between. It all started with us having met through a common friend, then went on to start a long distance relationship before finally making a decision on how we should push our relationship forward to the next level.

In Search for the Perfect Diamond

So going back to my proposal.

It was April 2016. I found myself spending hours and hours on the Internet and jewelry shops secretly searching for the perfect diamond ring for Joan.

This was because in about three months time, I’ll be flying over to the United States, to visit her in New York City and spend some alone and quality time with her before she finally moves back to the Philippines. I wanted to see where she worked and I’m curious what it was like to live in the Big Apple. All that was part of the plan that we both agreed upon about half a year ago when we talked about the future of our relationship.

Truth be told, searching for the perfect diamond ring is a daunting task. Not only is there a variety of choices, but it’s also one hell of expensive jewelry so you have to be sure to get the size that fits her and one that is her taste. You get only one chance so you have to do it right.

It was kind of fun and thrilling to look for an engagement ring which I thought she would like. However, as time passed by, I found it to be a huge dilemma because you get bombarded with a gazillion of choices for rings. There’s gold, white gold, rose gold, different karats. Not to mention that there are different cuts of diamonds. There’s princess, round, emerald, solitaire, cushion cut etc. It’s crazy.

Add to that is the pressure you feel about how much money you should spend on a diamond. People say that it should be worth three months of your salary. Well, not exactly nor necessarily. It could be much more, it could be much less. I think it depends on what you are comfortable with without going broke but at the same time not giving something cheap. It’s about striking that delicate balance.

Everything was confusing for me that time, but lucky for me, I have a jeweler friend who offered to come to my house to show me every type of engagement ring she has available and explain to me the differences of each. And because she was a family friend, it was easy for me to explain what I wanted for Joan.

It was then that I found this:

I thought it was perfect for her for a couple of reasons. One is that Joan is not really into loud and screaming designs. She prefers something classic: simple yet elegant. Something in which the diamond is given more emphasis. And so when I saw this, I knew that this was the diamond ring for her.

Preparing the Surprise

As soon as I had the ring with me, I knew I had one important task: think of a way on how I will execute the proposal when I get to New York.

I had a number of ideas at the time:

Idea #1: Propose on a private yacht while cruising the river surrounding the Statue of Liberty

I was searching for ideas on the Internet and location spots in New York City where guys usually propose and I stumbled upon a yacht company that offers a romantic river cruise in Manhattan, circling the Statue of Liberty on a sunset while having dinner.

It sounds amazing. No doubt. But the price? 1,000+ USD (and it didn’t include the taxes, service charges and mandatory tips yet). I mean, that would probably be okay if I was earning piles of cash, but given that I had to buy airline tickets to fly to New York City, buy a diamond and also prepare for the wedding in case she said yes – that amount would just be impractical. Also, wouldn’t riding on a private yacht look obvious that you will propose? So I decided to skip it even though I thought it sounded romantic.

Idea #2: Hire a tour guide photographer

One of the things I discovered while browsing New York magazines and travel blogs in the days leading to my flight was that there were several tour guides in Manhattan that not only toured you around but also offered to be your photographer as you walked the streets of the city.

These are pretty common in touristy places. The tour guides are not really professional photographers but they studied basic photography and they know the perfect spots in the city to take fantastic photos. They also know how to do those camera tricks that make you look like you are hugging the Statue of Liberty or holding the tip of the Empire State Building or what not.

The idea sounds brilliant if you think about it because the tour guide would act as a decoy or some sort of distraction while also serving as the photographer once you bend down the knee.

There was one problem though in doing this. Joan knew New York City in and out. I mean, she’s been living there for four years so she IS my tour guide. So I am pretty sure she would disagree with me when it comes to hiring an expensive tour guide when she knew better. The idea of it just wouldn’t fly.

Idea #3: Proposal at Times Square

One of the most popular places to propose is at the Times Square.

Remember that intersection in New York City, filled with bright lights, giant screens and huge billboards? Yes guys, it is that place where the New Year’s countdown and the ball drop happens in NYC. I thought that maybe this would be a great idea, after all, it is the place where proposals happen in the movies.

Whether this idea will work or not depends. “I’ll find out when I get there.” – I thought.

The Three Emojis and the Flight to New York City

Putting the location of the proposal aside, I set off to think of a gimmick on the actual proposal scene.

Questions that were brewing in my mind at that time were:

How would I execute the proposal?

What script do I have to say?

Will I connive with her friends?

What is my strategy to surprise her?

I struggled to think of something that I knew that would work. After all, I knew that Joan is the type of girl who:

A.) Does not want the spotlight and

B.) Does not want something cheesy, corny and exaggerated.

A day before my flight to New York City, I still found myself clueless on how to execute the actual proposal.

I stumbled upon a gift shop at Glorietta while shopping for stuff last minute that I would need for travel. In that gift shop, I found these…

Emoji wallets.

Maybe you’re wondering. Why emoji wallets and what will I use them for?

I bought three emoji wallets (or purses you can say) because I thought it was symbolic. For the past couple of years, our relationship was mostly long distance and Internet-based. What that meant was that most of the time, the only way we talked was through Messenger and the only way we showed how we felt (apart from the actual video calls) was through the use of emojis. I thought I can come up with something fresh, something personal, something relatable and something creative with these three emojis when I execute the proposal.

What that will be is something I still had to think about.

The next day, all my luggages were packed and I was at the NAIA airport with the diamond ring and the three emojis as I boarded the plane.

How and Where to Propose?

In 2016, Philippine Airlines already had a direct flight to New York City from Manila but with a layover in Canada.

The actual layover was in Vancouver before finally arriving to New York City. Total travel time (flight + stopover) was around 18 hours. It was such an exhausting flight!

During that long, Trans-Pacific flight, I was bored in the plane and had nothing to do so apart from watching movies, I began finalizing my ideas on how to execute the proposal.

First, I wrote three small notes and inserted them into the three emoji purses that I bought.

That was all I was able to do the entire flight. Because until I landed in New York City, I didn’t know what my strategy was – I still didn’t know how and where to propose.

See, the problem for me is that New York City is not my territory. It was Joan’s so she knew the best spots in the city: the fancy restaurants, the glamorous places, the coolest bars and the best attractions. She knew the exact places to go to and the ones to avoid.

That being said, I was at a disadvantage because I didn’t know the locations and the beautiful places to go to. Yeah, Google helps and TripAdvisor too, but who knew how the actual place would look like until you get there? A place might look good in pictures but the actual experience might suck and it could ruin my proposal.

Furthermore, Joan said she will be my tour guide in the city. So if I asked her to add a somewhat romantic venue I found on Google that was not originally in our plans and not part of the itinerary she created for me, she would begin to suspect and start having a clue about my proposal. I didn’t want her to expect because it would ruin the surprise, right?

To cut the story short, my plane landed in New York with me still having no plans on how to execute the proposal.

Taking My Chances to Propose

I’m sort of a planner kind of guy. Although I’m not as obsessive-compulsive as others who write down every detail of their life’s plans on their journal, I would pretty much say that I’m the kind of guy who instead had all my plans and to-do list in my head. I keep track of everything in my mind.

Since I already ran out of options on how to execute the proposal by the time I landed New York City, I thought that maybe, instead of planning ahead, this was the time for me to become more spontaneous.

So here was the thought, the premise and the final plan that I came up with:

I will propose at the EXACT time and EXACT place where I feel The Moment with Joan.

I didn’t know where and I didn’t know which part of the trip it would happen. I’ll just propose out of the blue as soon as I feel the magic.

Meeting at the JFK Arrival Area

Joan loves creating itineraries for trips. So at this point in time, she has already planned out all the places we will go to and the best tourist sites we will visit while we are together for the next two weeks.

She was excited as much as I was and the plan was she would pick me up at the airport as soon as I arrived.

As I made my way out of the immigration and into JFK’s arrival area, and having made up my mind to become more spontaneous, I thought:

“Well, what if I propose right here at the arrival area of the airport as soon as we meet?”

That thought lingered in my mind as I nervously worked my way to the exits.

However, as I thought more about it, the idea of proposing at the airport at 11PM NYC time, in a crowded place and with me not having a shower yet for the last 18 hours I was on the plane, did not seem like a good idea. Also, at the time, I was so preoccupied about freshening up and trying to look good for Joan by putting on perfume, combing my hair and thinking of the first words to say to her when we meet so I told myself: “Well, forget it. There are plenty of other places to propose so why at the airport?”.

When I got to the arrival area, I saw dozens of people waiting to meet their families and friends coming from different parts of the world. Then suddenly I heard a voice, “Hi Darling!” and saw Joan jumping to see me.

With all the things going on in my mind about proposing and wondering if I smelled good, the only words that came out of my mouth when I saw her were: “Hello, Kumusta?” (translation: Hi, How are you?), after which I gave her a smack on the cheek.

Joan laughed and said: “That’s all you’re going to say to me after not seeing each other for months? Haha, well it looks like you’re tired from your flight. Let’s go home!”

I replied saying: “Yeah that’s it. Haha”.

So we went home and slept. After all, it’s midnight already.

The Trip to Times Square and the crazy idea of bringing the engagement ring everywhere

The next day, we woke up early because Joan was planning to tour me at the heart of New York City: Manhattan, baby!

We were going to Broadway to watch Aladdin and to take photos at Times Square: the famous billboard-filled intersection.

I had an idea as we were preparing to leave the house that day.

“What if,” I thought, “that from this day going forward, I would bring the engagement ring with me (along with the three emoji purses) every single day WHEREVER I went with Joan? And if I felt that the timing and the place was right, then I would just bend my knee and propose wherever we were as long as we both felt the moment.”.

The idea sounded plausible and even brilliant to me.

It was risky because I may end up misplacing or even losing the ring since I’ll be carrying it with me around on tours every single day. But on the other hand, I thought that this would make the proposal special, spontaneous and even unexpected to her.

And so it happened. From her apartment, Joan and I rushed to go to the subway and made our way to the busy streets of New York City.

The city looked exactly as you would see in the movies. Busy, filled with people and a bit warmer than I expected. It was in the middle of summer after all.

As we walked and approached Times Square, I was getting ready with the proposal dialogue in my head and I started feeling my pocket to find the ring and make sure it was there.

I thought that if the timing and place looked right, I would propose even if we were in front of a huge crowd.

Unfortunately, Times Square at that time, looked completely obnoxious compared to the Times Square I had in my mind.

People were bumping into each other, road constructions were everywhere, cars and yellow cabs were rushing the streets and there was a lot of noise. It was hideous. There was simply no place for you to stop, kneel down and propose. People were rushing to the office and tourists were taking photos so if for some reason you block their way, they will shout at you. It was too crowded for my taste so I ended up not proposing to her and instead, we just took this selfie then went ahead to watch Aladdin in Broadway.

Fourth of July Rooftop Bar and Fireworks

I arrived in New York City in July 2016.

The timing was good because US will be celebrating their Independence Day on July 4th.

I booked a rooftop bar with Joan for the evening of 4th of July so that we could watch the fireworks as it lit the New York City skyline with the Brooklyn Bridge in sight.

I was thinking that the rooftop bar might be a nice place to propose because when you bend your knee, there will be fireworks lighting up the sky for Independence Day. It will look romantic. Or so I thought.

So I brought again the engagement ring with me when we left the apartment and hopped on the subway to get to the bar.

The bar we went to was fantastic and the crowd was pretty cool!

Like typical bars, the music was way load but it was hip. The place was a bit dark and moody. As we made our way to the rooftop, we ended up bumping with other well-dressed party people left and right. It was a nice place but we couldn’t understand each other because of the loud music being played, people talking and the exploding fireworks. The more I think about it, the more I felt like this is not the place to propose.

When we finally reached the bar’s rooftop, we saw the colorful fireworks piercing through the dark sky. It was amazing to see the fireworks behind the famous buildings and landmarks of New York.

While we were at the rooftop, it started to rain so I finally called it off in my head and said to myself, “Nope, this is not a good place and time to propose.”

We both enjoyed the night though. As a visitor in New York, I was thrilled to get a taste of what an actual bar or club feels like in a vibrant city like this.

Statue of Liberty

People say that New York City is and will always be a city for dreamers and believers.

Why? It’s because most people have ambitions to get there and as the lyrics of the song “Empire State of Mind” says: “If you make it here, you’ll make it everywhere”. That is the belief of anyone who aspires to travel and live in New York.

And speaking of all that, let me ask you this:

What is the most iconic symbol of New York City and no doubt THE landmark of the US?

It’s none other than The Statue of Liberty.

After Independence Day, we booked a trip to see Lady Liberty. She stands on a small island so we had to go there by a ferry boat.

And as usual, I was carrying with me again, the engagement ring. It was in a small pouch hidden deep down my clutch bag which I’ve been hiding from Joan since my arrival in the United States.

It was noon and we were on top of a ferry boat facing the Statue of Liberty. No other place embodies New York City than the exact spot we were in.

I was thinking whether to bend on my knee and propose. But it just didn’t seem to connect with me – neither with Joan just by looking at her face. I knew that no matter how symbolic the view was, it just doesn’t spell proposal to either one of us. Plus, we were sweaty and it was very hot that day so it just didn’t seem like it.

So I let the moment pass by. It was not our moment yet.

We just toured and tried to go up the statue, took some photos, ate at a hot dog stand and we called it a day. It was a beautiful day, but not a proposal-worthy day.

That Moment at Niagara Falls

The next morning, July 6, 2016, Joan and I woke up at 6 AM – about one hour later than we originally intended to.

It was chaos in the apartment. We were hurrying to take a shower, dress up and get our passports and plane tickets ready because we had an 8.20 AM flight at JFK airport.

We were flying upstate to see the world-renowned Niagara Falls.

Each one of us took turns to the bathroom to take a shower. We were hurrying because the airport is about a 30 minute ride from our apartment and the boarding gate will close about 20 minutes before the departure time. We didn’t want to miss our flight because our hotel had already been paid for in advance.

We each brought a small luggage with us because we will be staying there for just a couple of days before returning to New York City. As Joan was taking a shower, I made sure to not forget the most important thing in this US trip: the engagement ring.

We got to the boarding gate of our plane just 10 minutes before it closed. It was stressful but thankfully we made it to our flight.

One hour later, we arrived in Buffalo, New York – yes guys, home of the famous Buffalo chicken wings and the place where Niagara Falls is. We took a cab to our hotel which is close to the falls.

The hotel we booked was amazing. It was a Victorian-style Bed and Breakfast home. It looked elegant and romantic. Everywhere I looked and each turn I made I saw something whimsical.

After we checked-in, we dropped our bags in our hotel room, grabbed our wallets and our cameras then headed straight to the falls.

We were walking on the side of the gushing river which was leading to the falls. As we walked and took photos, I started to feel that this may be it. This might be the exact place where I will propose.

I’ve given it some more thought. The two more places which we intend to go to after Niagara was a fine dining and Three-Michelin-Star restaurant in New York City called Jean-Georges and the other was the viewing deck at the top of the Empire State Building. I knew that those two were absolutely great places to propose too. But as I looked over the magnificent Niagara Falls and heard the sound of the waters hitting the bottom of the lake below, it felt beyond compare. It was spectacular! The view was just too amazing and too breathtaking. There was nothing like it.

Just like the water from the river flowing faster and stronger as it approached the end of the cliff where it will plunge and become part of the waterfalls, my verdict, too, about proposing here became stronger. At this point, there is one thing I know and feel for sure: I will propose here at Niagara Falls or else this will be the BIGGEST regret of my life. The falls is just phenomenal and it was TOO GOOD to pass.

My instinct tells me that Niagara Falls would surpass every other place that we have been to or were going to. I was feeling confident and I knew that this was it. I could feel the moment and I think she was feeling it too.

When we reached the viewing deck where you could see the full panoramic view of all the three falls that comprise Niagara in all its glory and grandeur, we took an endless amount of photos. And then I asked Joan to sit on a bench on the viewing deck with me because I told her I wanted to take in and absorb all the beautiful imagery I was seeing. The scenery makes you believe that there is indeed a God that created all these so it makes you appreciate more the beauty of life. It was a sign.

When I came back to my senses, I knew it was the time to propose. It was now or never.

As we sat together on the bench, I pulled the three emoji wallets from my clutch bag one at a time, which, if you recall, was part of my proposal strategy.

I pulled the first emoji purse from my pocket and handed it to her. The purse was a smiley sticking out its tongue and one that looked like this: 😜

She asked, “What’s this?”

I said, “Well, just open it.”

She opened it and found a small note. In the small note was a question where I asked her if she was happy and if she enjoyed being with me on my New York visit.

After reading it, she responded by smiling and said “Of course.”

I handed her the second emoji wallet which was a kissing emoji and one that looked like this 😘

I asked her to open it.

She opened it and saw another small letter which read:

“Who would have thought that we are together now? We used to talk only in Messenger using emojis like these wallets, but now we see each other’s faces and we are no longer LDR…”

She just smiled and I knew she was starting to have a clue.

I pulled out the third purse. The third emoji purse had heart eyes like this one: 😍

It was the bulkiest of them all. It contained not only a letter, but also the box with the engagement ring in it.

I handed her the purse and I asked her to open it. She was smiling really wide as if she knew what was in there. She looked happy while I felt nervous the whole time. My heart was beating fast.

As she started opening the purse, she saw the box and the letter. She looked into my eyes because she knew what was coming.

Neil Strauss, author of the popular and bestselling men’s dating book called “The Game”, wrote one of the quotes that has inspired me in all areas of my life.

In his book, he said:

β€œIn life, people tend to wait for good things to come to them. And by waiting, they miss out. Usually, what you wish for doesn’t fall in your lap; it falls somewhere nearby, and you have to recognize it, stand up, and put in the time and work it takes to get to it. This isn’t because the universe is cruel. It’s because the universe is smart… it knows we don’t appreciate things that fall into our laps.”

Neil Strauss, The Game

In the last two years leading up to the proposal, Joan and I went from being mere Facebook friends, to being set-up on a blind date. From being in a long-distance relationship to something more serious. I knew we have come far, but I wanted both of us to take it even farther.

When I first started writing this story, I began by talking about how people believed in the idea that if something is for you, the universe conspires to make it happen. I think that statement is only partially true. For Joan and I, the universe helped because we had our common friend Gwen, who insisted on setting us up on a blind date and who we are forever thankful for. But without the effort on my side nor Joan’s side, things would have never happened. Because as Neil Strauss said, good things just fall nearby. You have to recognize it, stand up and put in the time and work it takes to get to it.

And that is exactly what I did.

And so, right there at Niagara Falls, in the midst of other tourists, the perfect weather, the scenic view and the sound of pounding water surrounding us, I kneeled, pulled the diamond ring out of the box and placed it on Joan’s finger. She opened the letter and as she started reading, I also vocalized and spoke to her what was in the letter.

“Darling, I Love You. Will You Marry Me?”

And with eyes and a smile shining brighter than any diamond, Joan looked at me and said “YES”.

*  *  *  *


After my two week vacation in New York ended, I went back to Manila. Joan remained in New York for a few months to take care of things she had to settle in the US before moving back to the Philippines for good.

In October 2016, she finally moved back to the Philippines and since then, we have never been in a long-distance relationship again.

We got married in December of 2016. Gwen, our matchmaker, was one of Joan’s bridesmaids of course. Here’s a sneak peak of our wedding…

Today, we live in Manila and are blessed with two handsome kids.

And that, my friends, is the story of How I Met the One.

Hi, my name is Chris and I am the founder of Pinoy Guy Guide. As a guy living in Bonifacio Global City in Manila, Philippines, I have a strong interest in writing about men's fashion, lifestyle, pop culture and gear for guys.

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