“I beg you to take a shot. Roll up on that hot chick in the bar and ask her out. On that good looking dude, and ask him to get a coffee. On your business idea, and make it happen. Because being 50, 60, 70, 80, 90, and having regrets that you didn’t swing the bat? That’s the worst of them all. Our bat is in front of us, TAKE A SWING.” – Gary Vaynerchuk
Take a swing is exactly what I did yesterday on my second to last day of my yearly Florida vacation. At the moment, I feel a stir of emotions ranging from happiness, sadness, and a little bit of sentiment. But what I can tell you is that I have absolutely no regrets. My goal as your dating coach is to hammer in a cliché lesson that we all lose sight of in our day to day lives: taking chances and living life your life to the fullest with absolutely no regrets.
Today’s story is about a girl I met a month ago on the job. Before you jump into any kind of judgment or conclusions, take the time to digest this story and see if you can find some lessons to help you improve your life, whether it’s in the love and relationship department, with your closest friends and loved ones, growing a pair and leaving the job that has been sucking the passion out of you, or pursuing your wildest dreams.
The Story – Part I
To give you some perspective, let’s take a step back to last month, Friday of the 10th of February, the weekend before Valentine’s Day. I was out at 230 Fifth Rooftop looking over the New York skyline with one of my friends and a client that I was doing a one-on-one session with. He was having a great deal of difficulty approaching women and working through the baggage of the last few years being out of the dating scene.
We originally started the night farther up in Midtown at another bar, but after 15 minutes at the first bar, we decided on 230 Fifth to continue the night and to make sure my client got his in-field practice for the night. It was a not so typical night at 230 Fifth and by that I mean it was unusually busy seeing that it had just snowed heavily the prior day.
I later remembered that it was Fashion Week, and it suddenly made sense why there were so many exotic looking male and female models on the line into the club. I wasn’t expecting to get in but nonetheless tried anyway with my client and friend in tow. Surprisingly, we got in because the bouncer working that night was a friend that I had made over the years of trying to sneak into the joint as a curious pre-21 year old to now as a veteran dating coach.
As the lines were being divided up to get into the elevator to get to the top floor, I encouraged my client to head up as there was one more spot left on the elevator. He went up first while my friend and I stayed behind to wait for the next elevator. The next one came and I crammed into it with at least 8 other people including my friend. The elevator was quiet, but nonetheless I made a joke about our current situation, to which everyone in the elevator started laughing.
I immediately noticed this pretty young Hispanic looking girl looking at me and just giggling. I couldn’t help myself and suddenly the switch just went off and we just started talking and flirting. The elevator opened up, and she went ahead with the crowd in our elevator and I went with my friend to go find my client.
As I found my client and saw him in his nervous state, I started pushing him to warm up and get his practice in. We approached multiple groups and ended up running into the girl I was flirting with in the elevator. We talked and flirted a bit more, but because I was on the job, I couldn’t and wasn’t going to neglect my client. I approached another group and hooked my client in.
Everything was running smoothly, so I decided to take the opportunity to take a step back and go find that girl again. I eventually found her and we just picked up where we left off. I moved her to the bar and I bought her and her friend a drink, and we moved back up to the rooftop where it was quiet and more intimate. I found out that she was only in town for a few days, and that she was originally from Tampa, Florida and was leaving on Monday.
I had her add herself on my Facebook, and as I was about to punch my number into her phone and have her punch her number into my phone, I immediately got a phone call from my client who was in a panicked state. I had an obligation with my client, so I cut it off quickly, kissed her on the cheek, and hugged her with the intention of meeting up again.
The night ended after having a motivational pep talk with my client and pushing him harder at the next bar we went to. After he had left and I regrouped with my other friend, I messaged her, apologizing for disappearing and asking her out for brunch on Facebook, not expecting any response. Two days later on Valentine’s Day, I got a message from her. She wished me a Happy Valentine’s Day with her number attached to it.
She was back in Tampa so we couldn’t meet up or do our planned brunch. It suddenly hit me that I was going to be in Florida for the entire month of March for my yearly family vacation. From that point on, we started talking to each other via social media, ranging from texting, to Snapchat, and Facebook messenger. I had told her I was going to be in Florida for the month, and we started making plans to meet, hang out, and adventure through her neck of the woods.
The Story – Part II
I arrived in Florida and had just taken the first two weeks of my vacation to decompress, relax, and intermittently do my grad school work and Craft of Charisma projects. We couldn’t meet anyway because she was going to be away for the first week and a half of March to visit her family. We both decided to make plans when she got back. In the meantime, I focused on catching up on reading, working, exercising, enjoying the nice weather, and trying to be productive.
Fast forward to the beginning of this week… She was back and we started making plans. We had both decided to meet up on Friday the 24th with a day planned to hang out, relax at the beach, grab some fresh seafood, and do a little bit of sightseeing. I had no idea how I was gonna get to Tampa, since it was 200+ miles north of my location, and my parents had been using my car and were skeptical about my motives, because ever since I was a kid up until now, I’d always get myself into the craziest shenanigans.
My college years taught me one of the most important and valuable life skills – the fine art of bullshitting your way through life with creative thinking. I made up a story about a friend of mine from Rutgers who moved down to Tampa for work. I told my parents that I needed the car for the day because we hadn’t seen each other since graduation and wanted to hang out and catch up on things.
They told me to tell my friend to come down here, since it was risky for me to drive all the way up there and that they needed my car. My stubborn and focused mind wasn’t going to stop and when I say I’m going to make shit happen, it happens by any means necessary. This time was no different. I looked for the best deals on rent-a-cars in the area and I stumbled upon the Uber version of car rentals, Turo.
It was my first time on it and I was skeptical because the pricing was so cheap to rent a car. Nonetheless, with a little bit of research and reviewing, I found myself giving the app the benefit of the doubt and renting a car from a complete stranger, knowing full well that if anything happened to that car, I was subject to taking on all the risk. I booked the car, told her I was coming up, and told my parents that my friend was coming to pick me up from our vacation home.
With a plan in place, my dad, being the typical Asian dad, was insistent on meeting my “friend” and finding out exactly where “we” were going for the day. I deliberated for the Thursday before our adventure on what to do. So I decided to pull the old disappearing act I always used to pull in high school when my parents tried to make me attend our entertainingly dysfunctional family reunions with our extended family or to get out of running ridiculous errands.
The following day, I woke up at the crack of dawn, took an espresso shot, packed my go-bag for the beach, said goodbye to my mom, put my shades on, and bolted out the door before my dad could ask me where I was headed to and get suspicious. Our house is situated in a gated community, and it was a long five mile walk from the house to the gate. Even though I’m in pretty good shape, the walk was exhausting.
I made it to my Uber and after getting to know the driver, talking about his family and sports, he kindly went out of his way and dropped me off at the driveway where I was supposed to pick up my rent-a-car instead of the designated location I had set. After meeting the rental owner and playing with her dog, I got in the car and hauled ass on my way up to Clearwater Beach. It takes a lot to get me excited these days, but feeling like a pre-pubescent teen again, I just rolled with it and drove the 200 mile, two and a half hour trek to her.
After a few bathroom stops, hitting some traffic, taking a few loops and turns, and asking the locals for directions since the GPS on my phone was going haywire, I made it to Clearwater. I took my rent-a-car and parked in a pink hotel parking garage based on her recommendation. I got out of my car, fixed my hair, and grabbed my bag. I hopped on the elevator and started walking towards the beach.
After taking a few snapshots of the beach, as I was about to call her, suddenly with perfect timing her number started buzzing on my phone. I answered and she suddenly popped up in front of me with her hair tied up in a bun and in a lovely bikini and with her friend in tow. We walked and talked as we decided to get some seafood for lunch. We had crab legs and coconut shrimp tacos, and as a seafood addict, I can say that they were the freshest crab legs I’ve had in a while.
We sat together, flirted, and talked. She told me she was seeing somebody but that it wasn’t serious. I really didn’t pay much mind to it and just enjoyed being present with her. After lunch me, her, and her friend started walking towards the beach. Her friend wanted to try out this bungee cord trampoline. I forgot to head over to the ATM and I didn’t feel like hopping on cause of the shit ton of crab legs I had just eaten.
I encouraged her to hop on, but she had sprained her ankle not too long ago and decided to just chill. After seeing some young teenagers catcall her and her friend, we moved onto the beach, set up shop with our towels, ran into the water for a moment, came back, popped on the tanning lotion, and laid out in the sun. After 10 minutes or so, her friend left, and for the rest of the day it was just me and her.
Besides the funny snaps between her and another friend of hers that was supposed to meet us, we spent the rest of that time getting to know each other a little better. We both fell asleep on the beach together. Being the workaholic that I am, it was truly the first time I’d been able to completely relax without worrying about anything work related. We both toasted like bagels as we napped away on our beach towels.
I woke up after maybe 20 minutes of toasting and convinced her to go in the water with me despite her not liking how cold it was. At this moment, I tried to hold her hand to lead her to the water, and she just interlocked her arm with mine and we went in. I splashed her, as much as she hated it, and she did the same with me. We went back and I tried to hold her hand again.
She told me again about the guy she was seeing and that she didn’t want to feel like she was cheating on him. As a guy who’s been in this game for a while, I’m no stranger to this at all. Even though I was clearly attracted to her, and to be honest didn’t know how she felt or where she was at, I decided to listen to my gut and just respect her boundaries and not persist towards something that would make her feel or regret our time together.
We continued the rest of our adventure sightseeing around the pier, learning about each other’s lives, our quirks, flirting with each other, and sneaking into a hotel pool together à la “Catch Me If You Can” by ironically pretending to be a couple staying in the hotel. We found a set of beach chairs and I set on to get us a round of drinks while we laid out on the chairs overlooking the gulf and the beach.
In that time frame, we talked about our passions, dreams, and the craziest adventures we both had been through. She told me a story that had just resonated with me and ironically goes hand in hand with the theme of this blog post. It was about her mom characterizing her open-minded and adventurous personality, “You live your life as if you’ve been diagnosed with terminal cancer.”
At the heart of it all, it resonated with my life philosophy of owning who you are and grabbing life by the balls. I felt really comfortable around her and I couldn’t help but just look at her and appreciate her natural beauty and her sweet and easygoing personality.
After slamming back a couple more rounds of drinks, listening to our diverse Spotify playlists, and enjoying the view, I noticed a higher observation deck with a better view from our spot. We both decided to attempt to sneak in and get few pictures together for memories and Instagram. After reaching the top floor and seeing that it was locked, we decided to just chill out and wait for someone to open the door so we could both sneak in together.
A group of spring breakers burst through the door and we both took the opportunity to sneak in and see the view. I asked this older lady to take a picture of us. After a few attempts and moving away from the sun, she finally copped a few good shots. It felt ironic and funny, here I was reconnecting with a total stranger that I had met a month ago before Valentine’s Day on a rooftop in the freezing cold with a pile of snow surrounding us, to a month later on another rooftop being surrounded by white sand and dressed in beach wear.
The sun was starting to go down and we decided to bolt out of the hotel and figure out how to pay for my parking garage fee. We went into the gift shop based on her suggestion to pay for the ticket, and the lady directed us to the front and suggested that we pick up some chocolate to get our parking discounted. I decided to take the opportunity to buy some Advil since I had a mild headache from my lack of sleep the night before.
It turned out that we had to pay for our ticket in the garage, and as we paid for the chocolate and Advil, I teased her for setting me up to buy her some chocolate. She wouldn’t stop laughing and she lead us both to taking the stairs to get to my car. I wanted to take the elevator but she wanted to burn calories.
To make a long story short, the stairway reeked of urine and trash; it reminded me of the NYC Subway. So despite the funny setback, I had a piece of home at my feet. We got to the floor where my car was parked and the door was locked. She wouldn’t stop laughing and it looked like she was getting an ab workout from all the laughter, plus each floor was locked until we got back to the urine stenched floor and just walked through the slightly cracked open door.
We finally made it to my car, and on that long car ride back we sang along to the songs on her playlist. We made it to her car and she showed me where she worked, the iconic and original Hooters. I followed her back to her home and after a long cat and mouse chase on the highway, we got back to her place. She introduced me to her family, her cat which is the first cat I’ve ever played with that wasn’t anti-social, and we ate some homemade Arroz Con Leche.
After the adventure of the day, we were both completely spent, burnt, and exhausted. I decided to pass up on going out to another bar with her and her friends, since I get enough of that back home. I decided to call it a night since I had a two hour drive ahead of me. She walked me to my car and we hugged and I gave her a kiss on the cheek. I thanked her for her kindness and appreciated the time we spent together.
I started my two hour trek back home, and spent the bulk of that speedy drive down the interstate reflecting on the day, listening to “Time” by Pink Floyd, and letting the raw emotions digest inside of me. I felt happy and sad at the same time, but most of all the key takeaway of it was that I had absolutely no regrets.
I’m completely aware of the fact that this post was a little unconventional and some of the things I did throughout this story contradict some of the dating advice I’ve given in the past. At the end of the day, it’s not always about holding hands, make outs, foreplay, and sex.
One of the biggest questions I’ve always gotten from my former clients, even after they’ve been playing the field, have had tons of endless and raunchy sex, and have been going out and honing the skill sets we’ve taught them, they lose sight of the whole reason why they got into it in the first place and struggle to find love and feel intimate.
It’s all about ending your loneliness and genuinely connecting with someone. In life, whether its finding love or doing something you’re passionate about, it’s important to take charge of it and make the most out of the opportunities that pop up in front of you. My point is, don’t fear failure, fail gracefully if you have to. Think of what you want to do and execute it. It’s that simple.
A lot of what I did didn’t make any logical sense. Did I have to reach out and reconnect with a random stranger I had met while I was working? Did I have to go through the trouble of crafting a ridiculous alibi and renting a car from a random stranger through an app I’ve never used before? Did I have to drive 200+ miles to a random city I’ve never been to in my life? Did I have to spend my entire day at the beach with that same random stranger who I’m attracted to after she made it clear that she was seeing someone despite wanting to hang out with me?
The answer to all of those questions is no. While I didn’t have to do any of those things, I’d rather stay true to my principles and live a life well spent on making things happen, taking chances, having no regrets, having random and adventurous experiences, and meeting and connecting with people at the core of it all.
To quote Ferris Bueller, “Life moves pretty fast, if you don’t stop and look around once in a while you could miss it.” Nothing in life is guaranteed, whether it’s your career, relationships, or health. While we can’t control everything, it’s important to take those opportunities and say yes to every experience and gut feeling that that comes along.
Despite all of that, I genuinely enjoyed her as a person, her company, and connecting with her. After spending the day with her and walking away from that, it left me with a feeling of ambiguity, but also a feeling of fulfillment, and another adventure and notch on my list of random life experiences. What I forgot to mention was that random experience and adventure into an unknown territory made me feel alive.
While I can walk away and not know what the road has in store, it really makes the journey more exciting and worthwhile. Take those chances while they’re in front of you. Go say hi to that cute girl you’ve been eyeing, apply to your dream job, swim with the whales, jump out of a plane, and most of all listen to your gut and live your life, because no one else can live it for you. Think, execute, fail gracefully, be grateful, enjoy the ride, and make life happen.
‘Til next time… Take care for now, we’re always here for you guys!