This is the first chapter I wrote in this book. I wanted to start with this moment because it changed everything.

I walk into a surf shop in San Juan, Puerto Rico. I am hungover, feel like garbage, reek of alcohol, and look exactly how you would imagine someone on a multi-day bender would look. As my eyes adjust from the bright Caribbean sun, someone greets me in Spanish.

"I'm sorry, I don't speak Spanish."

"Welcome. Let me know if I can help you find anything."

I look up and see a beautiful Puerto Rican girl standing shyly with the most adorable smile. It is hard to describe the feeling I had at that moment, but I knew somewhere deep down that my world was about to change.

I try to play it cool, mumble something back to her, and awkwardly meander around the surf shop. I pretend to browse the surf gear, but can’t stop glancing at her. She looks familiar, and I want to talk to her. I make three or four approaches and wave them all off in a panic on short final.

I'm embarrassed to admit this, but I had recently read "The Game - penetrating the secret society of pick-up artists." by Neil Strauss. I assure you that if picking up girls was an art, my preferred medium would have been finger painting, spilling paint everywhere, and ruining my clothes. This book gives me some courage, and I develop a plan.

There are several large locked display cases of sunglasses in the front of the store. I harness my inner pick-up artist, strutt to the sunglass case, and stand uncomfortably while trying to look as cool as possible.

"Would you like to see some sunglasses?"

I nod and utter, "Yes, please."

My plan is coming together.

 Over the next half hour, I try on nearly every pair of sunglasses in the case. In between each pair, I attempt small talk. I ask her about surfing, ask her opinion on at lease 60 pairs of sunglasses, and tell stupid stories about the parking tickets I earned in San Juan. I try to make her laugh because I can’t stop admiring her smile. I talk to her about everything, except the one thing I want more than anything….to ask her out. After boreassing her time for a quarter of her workday, I decide it was only fair to settle on a pair of sunglasses, hoping she would receive a small commission.

She brings the glasses, which I didn't need nor intend on wearing, to the counter, and I remember an important principle in "The Game" - time gapping. This is when, for some unknown reason, you give the person you're attempting to pick up some space. I think the theory is that you would leave them wanting more interaction, and this somehow improved your chances of success. I tell her I want to keep shopping, and I hit the flip-flop rack for no reason, despite having awkwardly fumbled around with the same flip-flops 30 minutes earlier. I am becoming a proper pick-up artist. I'm not sure about post-time-gapping success statistics, but I use the time to devise a plan.

I live in Isabela, Puerto Rico, on the West side of the island. It is a short 2-hour drive from San Juan on the most treacherous confusing highway in the world. The West side of Puerto Rico is home to several world-class surf spots, and I am right in the middle. I live in a beach bungalow, and the downstairs is a vacation rental always packed with surfers.

After "time gapping", I strut to the checkout counter to pay for the sunglasses. I casually mention the surf rental and use it as an excuse to exchange phone numbers. I am almost there, I just needed to ask her out!

I fail.

I am too scared and walk out of that surf shop with my tail between my legs. Defeated. I drive off in my Jeep telling myself, "At least I got some new sunglasses." I am disappointed in myself. Some pick-up artist I am. I start driving home. I miss my friend. I feel stupid for wasting money on the pick-up artist book and now on sunglasses!

Then it hits me again, a strange feeling that the world is telling me I have to do something. I have her number, and I’m not ready to give up yet. I’m not ready to spend the rest of my life wondering about the girl in the surf shop. I pull over.

Time stops. I wait desperately hoping for an answer, hoping my fear didn't stop me from ever seeing this girl again, hoping she didn't give me a fake number, and hoping that walking out of that surf shop wasn't the worst mistake of my life. After a painfully long 5 minutes of staring at my phone and envisioning everything that could possibly go wrong…

Ok. At least she didn't give me a fake number. Her response is factual, but doesn’t answer the question. The stress continues as I stare at the phone and hope for clarification. After what seems like another eternity, I craft the perfect response.

I may not be a pick-up artist yet, but I am crushing it with my text message game. Surprisingly, she doesn’t answer right away. Maybe she is familiar with time-gapping and is using it against me? After another excruciating 5 minutes…

That's it?!?! I'm still illegally parked on the side of the road in San Juan trying to figure out what to do in this scenario. "The Game" did not cover text message interaction, and I feel ill-prepared. Is she interested? Is there a language barrier? Do I reply right away? How long do I wait? I Don’t want to seem desperate and ruin it. I wait for what I think is the proper amount of time to avoid looking like a stalker and send this…

Just answer! I can’t take much more stress. This is now the longest she’s made me wait.

Another question?! Is this a test? I will literally go anywhere just to see her smile again, but I heed to play it cool.

I Can’t believe it! I am given a second chance, and I’m excited. I celebrate in the car and rush to a pharmacy to grab deodorant, breath mints, and some water, hoping I can kick my hangover and look like a presentable gentleman for my big date!

A few minutes later, I arrive at the surf shop and pick her up. At this time, I am still unclear about her name. When I asked earlier, she said it with an abundance of Latin flair.

"Nah-Tea"

"Naughty?" (That can't be right)

"Naww-Teee"

Certainly, nobody would name their child naughty. I pretend to understand and move on. "Ohhh, got it. Naughty."

Anyhow, I pick up "Naughty" and ask her where she wants to eat. She says she is a vegetarian, and luckily, since I have stopped eating meat, I know a vegetarian spot nearby. I don't remember what we talked about at lunch. Despite the emotional roller coaster I went through to be on that date, I remember having fun, laughing, and feeling totally comfortable with her.

Towards the end of lunch, her boss calls, and she excuses herself to take the call. I fear the worst. I am convinced she is going to pull the "work is calling, and I need to get back right away" maneuver. I prepare myself. To my surprise, her boss had called to say that it was slow at the store, and she could have the rest of the day off. Inside, I am ecstatic, but on the outside, I play it cool like the pick-up artist I am. As we are finishing lunch, I tell her I have no plans for the day and could take her back to work, or we can keep hanging out. We decide to immediately go on our second date.

It starts pouring rain, and "Naughty" wants to see "Easy A," starring Emma Stone, a high school romcom and modern interpretation of "The Scarlet Letter." We drive to "Plaza las Americas," get tickets for the next show, and settle into our seats. We are a few minutes early, and as we sit there, we make our relationship official by following each other on the socials. Luckily, this clarifies a few things. First, I finally realize that her name is Natalie, and she goes by "Natty" because she thinks it sounds edgy. Second, I finally realize why she looks familiar. Her socials are full of pictures of her surfing, and I realize that I had seen her at the beach weeks before. I nearly drowned a few times, being hit by waves, mouth open, sitting on my board as I watched Natalie surf. She is a phenomenal surfer and was a joy to watch. I had told all my friends that I fell in love with a surfer girl at the beach that day. I can’t believe I am sitting beside her in a theatre on our second date!

We sit through one hour and thirty-two minutes of high school rom-com bliss, and our second date is over just like that. As we leave the theatre, I ask her again if she wants me to take her back or keep hanging out. I tell her I know an Italian place in Old San Juan with authentic Italian food and the best mojitos I've ever had. Soon after, we are walking through the charming Old San Juan streets on our way to our third date. It seems like a fairy tale, and I already feel like the luckiest man alive. We eat some Italian food and drink too many mojitos. We stumble around San Juan, dance, laugh, and have the time of our lives.

I am in no condition to drive, so I book a nearby hotel, and we stay together. In the coming weeks, I will spend every minute I can with Natalie, driving back and forth to San Juan just to spend a few hours with her. A few weeks later, I ask her to move in with me, and we have been together ever since.

We couldn’t have known it at the time, but we needed to find each other because we were both about to go through some of the most challenging, traumatic years of our lives. Our relationship would quickly be galvanized by the pain of loss.

Natalie tells a different version of this story. If you ask her, she usually goes on a tirade about how she wanted nothing to do with me because I had a cut on my foot. A few days before I met her, I had nicked the top of my foot on my fin while surfing and had a large gash. I did no first aid, so the cut didn't look healthy, but that wasn't the issue. At some point during the marathon sunglass tour, she noticed the cut, and I told her it was a surfing injury. That apparently set off alarm bells, and according to Natalie, "nobody that actually knows how to surf would cut the top of their foot while surfing." To this day, I am not sure what kind of CSI wound analysis she used to determine this, but being a kook, or someone that couldn't surf, was an immediate deal breaker for Natalie.

Natalie also recounts that I wasn't "her type ." She loved scrawny, long-haired, soft-looking, emo, Chris Angel, eye makeup-wearing, My Chemical Romance listening type. As a bald man whose most recognizable feature is a permanent mean mug, there wasn't an immediate attraction. Despite my charm and the various techniques I learned in my book, I didn't stand a chance.

Natalie had recently escaped a two-and-a-half-year relationship with a physically and emotionally abusive partner. She had been single for a couple of months and swore she would be for a while to recover from everything she endured. When I texted Natalie, she showed it to her coworkers. Knowing what she had been through, they urged her to say yes and go out with me because I seemed nice. So as I sat in a panic waiting for her to text me back, she was arguing with them about why she couldn't possibly go out with "some gringo” because of the whole cut foot kook situation. Eventually, she relented and texted me back.

The ultimate Puerto Rico vehicle is a Jeep Wrangler. The moon has fewer craters than the Puerto Rican highway system, it's always warm enough to have the top down, and many of the best surf spots require off-road capabilities. In Puerto Rico, it is not uncommon to see traffic backed up for miles because proud jeep owners will drive 20 mph under the speed limit in impromptu parades to showcase their lifted steeds. Natalie had always wanted a Jeep Wrangler. It was her dream car.

I had no idea as I pulled up in my lifted Jeep Wrangler, the ultimate surf safari vehicle, Natalie would take it as a sign from the universe to give me a chance. That second chance got me to lunch, and after talking her ear off, she believed I was harmless and kind. A kind man was all she wanted at that point in her life. After lunch, our stories of that day corroborated, and we often reminisce about our first moments together.

Despite how different our stories are, we both agree that it couldn't have been luck. I'm not religious, and I'm not sure I could explain what I believe in, but meeting Natalie makes me think there is more to life than luck and coincidence. To this day, I can't explain how I ended up in the surf shop. I had just dropped my friend off at the airport, was trying to take a shortcut, spotted the surf shop, and something told me I should go in there. Natalie had been promoted the week before to a data entry position and no longer worked in the front of the store. That day, someone called out, and she reluctantly filled in at the front of the store. She assumed her up-front position mere minutes before I stumbled in with my cut foot. Those are just a few of the final things that had to go right to put us in each other's paths. This plan had to have been put into motion years before. I almost didn't make it into the Coast Guard Academy, should have never made it to flight school, and barely made it through, was selected for helicopters, got orders to Puerto Rico, and happened to drop my friend off at the airport that morning. Before walking into that surf shop, every moment in my life had to go exactly as it did, or we would have never happened. I can't accept that it's just luck.