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How an Introvert Dated 50 Men in New York City in Six Months

by Aboelez 28 days ago in single
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I was a late bloomer. Socially awkward. And an introvert.

How an Introvert Dated 50 Men in New York City in Six Months
Photo by Nick Fewings on Unsplash

In kindergarten, I had selective mutism. Words would freeze in the tunnels of my vocal chord, entangled in five-year-old wonderment at the big wide world. I would approach Miss Casteñeda’s wooden desk, eager to show off a perfectly cut out heart or my artwork of birds and trees and castles. I wanted to tell her how I tried so hard to color in the lines this time, but my words always lost its voice mid-flight. Most days were a failed quest to transform my thoughts into words into speech.

Middle and high school consisted of more socially awkward behaviors. My friends were other socially awkward peers, the ones who didn’t quite fit in with the athletes or the scholars or the pretty girls. I powered through college in three years because the social culture of collegiate life felt like a violation of my personal space. It was never my thing.

I’m that girl who will choose leisure time alone, dinner with a small group of friends, a book over a party. Every time. Small talk makes me want to vomit. Some say that I’m reserved and distant in communication, that it’s hard to crack me. Friends and strangers, alike, diagnosed me with BRF. It’s true. I’m charming like that.

The introversion fit in nicely with my family’s conservative views on dating. My parents emigrated from China, via Hong Kong, when I was two years old, with big American dreams for me. Allowing their daughter to date and divide her attention between school and boys was never an option.

We were to adopt American riches, but not American dating culture. At senior prom, my dad unexpectedly showed up, still in his apron (stains and all), before the night was over to pick me up. Male friends were seen as ominous threats to my virginity and future. The rule was, plain and simple, no dating until my schooling was complete. And when the time came, they would fulfill their parental duty of choosing a suitable husband for me. Preferably a banker or a doctor or a lawyer. Definitely an Asian.

Soon after college graduation, exactly on schedule, my parents asked, “So, when are you getting married and starting your own family?”

I was half horrified, half amused. Was I really expected to go from zero dating experience to marriage and kids? Who does that? Well, not surprisingly, they did that. And their parents did that. And their parents’ parents did that. And now, it was my turn to do that. They were pining for the grandchildren that I was a good 10 years away from producing.

In spite of my objections, they set up dim sum meet and greet dates with eligible bachelors, recruited through the family’s extensive network of aunts, cousins and friends. The pressure to find a husband on their timetable was simultaneously comical and intolerable.

So, here’s what I did. I ran from the pressure and crossed the Pacific to live abroad for a few years. Take that, parents.

In the anonymity of a new city, untethered from my family’s narrative, I became bold in little ways. I struck up conversations with strangers, connected with fellow late bloomers and introverts, and you know what? I was actually witty and charismatic. Even hilarious when I wanted to be.

It’s true. 100% introvert.

It wasn’t until my late 20's when I embraced my introversion. Reading literature by Susan Cain and Anneli Rufus helped me to understand my quirks and be okay with being that girl who would rather kick back with a book and a glass of wine on a Friday night. Prior, I was always uncomfortable with this defining aspect of my identity. It was like an itch I couldn’t scratch away.

Solitude, wrapped up in the comfort of my own thoughts, is where I feel at ease and energized. Solitude is my default.

When I was ready to start dating again, I moved back to New York City, a little stronger, a little smarter than before.

Those first few dates were comical. I met a genius chemist who walked his cats around Prospect Park every morning. Another man took me to Henri Bendel on 5th Avenue for free cupcakes and champagne. Another tried to feel me up during tapas and sangria. During bathroom breaks, I sent my friends hashtag poetry conveying disappointment in the city’s line up of bachelors: #timesaretough #iwanttodie #justshootme.

Turns out, I missed the big fat memo that dating in New York City was not easy. Single women outnumber single men by about 150,000. It wasn’t just a ratio imbalance, but the overall dating culture was a bit fast and furious. My city is one of the top cities for single men.

Blue blobs for men. Salmon blobs for women. You do the math.

So, what does a woman, who scores 100% introvert on the Jung Typology Test, do when it comes to dating…in New York City? I was entangled in 31-year-old bewilderment at the big wide world of dating in New York City. But hey, I tried.

For the next year, I dated a few men, quit, dated a few men again, then quit again. A few good to great men showed up in the mix, but no one with long term potential. “Finding a good man” seemed as elusive as finding a good no broker fee apartment in the city.

It’s me, I deduced. I’m too socially awkward, too introverted, too inexperienced. Remember that Friends episode where Ross flirts with the pizza delivery girl by talking about how an odor is added to gas as a safety measure? I was girl-Ross.

In Outliers, Malcolm Gladwell discusses how it takes 10,000 hours of practice to achieve mastery in a field. Chess masters, programmers, and world-class violinists all flourished, not by virtue of innate skill, but by life factors which allowed them to simply log more hours of practice. Thousands more hours.

Since dating didn’t come naturally to me, maybe what I needed was more practice. Maybe I needed to compensate for the dating practice I missed out on during adolescence. It’s not that I wanted to be a master at dating; I just needed to demystify dating for myself. Would I know a good thing when I saw it? Would I recognize love when it was present? What are the true non-negotiable qualities when considering a life partner?

And that’s how the 50 Dates Quest was born.

It was a personal quest to investigate those questions and more. Starting May 13, I committed to going on 50 dates for the next six months. Pretty ambitious for an introvert.

Setting Up

I signed up for Tinder, OkCupid, and Match.

I kept a running record to document basic information about their name, hometown, age, and a few standout comments or quirks.

I gave out my Google voice number and organized names on my contact list by their first name, preceded by an A. This way, I didn’t inadvertently engage in dating banter with my friend, Josh, when it was meant for A-Josh.

Two Simple Rules

Transparency is gold. If a date asked how Tinder/OkCupid/Match was going, I told them about the 50 Dates Quest. Most took it well, relieved that I wasn’t pining for a relationship. Others were more sensitive, as if sizing up how they ranked amongst other men.

I always offered to split the bill. Not to be some 21st century independent woman, but it seemed like a fair thing to do if I was going to power through these dates. (Only one date took me up on that offer.)

That’s all. Just two rules to start with. Without much pretense or expectation, I dived into these dates, making up other rules as I went.

The Dates

Before we start, I know that men are more than just numbers, but for the purpose of anonymity, I will refer to them by their order in the 50 Dates Quest.

Now, let us meet a few of the fellas. Number 1 was a stocky Albanian. A man’s man. Mr. Casanova. He told me that tonight was my night. We could go wherever I wanted, do whatever I wanted. Over tapas at Boqueria in Flatiron, he told me that he once popped a Viagara pill that made his heartbeat so fast, he thought he was going to die. TMI but moving forwards.

There was Number 3, a cool cat who grew up in a kibbutz in Israel before moving to South Africa as a teenager. He was a musician who served his three years in the army and landed in the city after a year traveling the world. He knew the best place in Manhattan for shakshouka. I loved that he was an open book.

Number 5 was a handsome Irish man. He loved his job as an engineer, working with medical researchers to develop new tools for surgery. He was witty, intelligent, and well-traveled. The conversation was easy.

Number 8. What can I say? Eight was great. He was the first American I ever dated and the first to ask how the dating was going. When I told him about the 50 Dates Quest, he shared that he was newly out of a relationship and not ready for anything serious. He was Mr. Social Media, a bit socially awkward and charismatic. I loved the way he said Hey girl. I think it was the mutual lack of attachment to anything serious that allowed us to relax and acquaint ourselves with each other with ease. It was a mixed blessing that he lived on the west coast because I think I would have fallen for him too hard, too fast.

We’ll get back to Number 8 in a bit, but for now, let’s move it along.

Number 9 was a taxation lawyer, a Brooklynite who dominated the conversation with obscure facts about Tibetan dreams while I munched on coconut French toast and poached eggs. I lost him at hello. I had to end the date early. Remember how introverts are with this kind of stuff. Not good.

Number 11 was a French dude, smooth in all his French ways, a typical finance worker. At the end of the date, he said, hey, let's go back to your place. I wondered if I was giving off a sexually open vibe or if he just assumed that getting laid was part of the deal. Either way, I left him on the corner of 5th Avenue and 18th Street. Just like that.

Now, friends, at this point, I’m feeling the need to retreat. A month into dating, the messaging back and forth, the looking cute, and the being all charismatic wore me out. But I keep on keeping on, because the story can’t just end at the corner of 5th and 18th.

I knew I would be out of town for the next month, so I went speed dating, something I never thought I would do, to not fall behind. My comfort zone was now a pinprick in the distance.

At a bar, on Crosby Street, 50 women were stationed at small intimate tables that ringed the room. The pool of bachelors ranged from graduate students to young professionals, to tourists. It was all there. Every five minutes, at the signal of the host’s bell, 50 men moseyed onto the next lucky lady. Candles and lively jazz music set the mood.

Each rotation came with a flurry of typical questions. So, where are you from? What do you do? Do you have any siblings? Some men, trying to jazz up the conversation, prefaced their five minutes with, I know you’ve had to answer the same boring questions, so I thought I’d ask something different. If you knew you were going to die tomorrow, how would you spend your last day? (Obviously, not speed dating).

I went into the event with an open mind. Honestly, I tried. I’m sure that in that little treasure trove were good men, but after 26 five-minute dates, I was utterly drained. I left at intermission and didn’t bother logging on to match with any of the men.

26 five-minute dates; Joshua circled himself.

Remember that part about me making up the rules as I went along? Well, I counted all 26 speed dates, because you know what? Speed dating still takes time and effort. If you’re like some of my more judgmental friends, you probably think that’s cheating, but I hope you can find it in your heart to empathize with me. Either way, I was the one making up the rules.

Dating was officially whooping my ass. I was getting spanked. And not in the good way.

I took a few weeks off to recuperate. I wasn’t completely dormant though; I used the downtime to screen potential men for the next round of dates. Over the course of six months, I perused thousands of profiles on the three dating sites.

On the train, on lunch break, on the toilet. Anytime I had a few minutes to spare, I was swiping or reading profiles. Let’s say an average of 20 swipes/profiles a day, 30 days a month for six months. That’s a total of 3,600 men. Out of those 3,600 profiles, I disregarded about 98% based on their tag lines, party/dog/drinking/selfie photos, lame messaging banter, or other equally superficial reasons. That narrowed it down to about 72 potential dates to engage with.

It may seem like No Big Deal swiping left or right on these simplified apps, but screening was a part time job in itself. If you’ve experienced the joys of the latest dating apps, you will be familiar with the following types.

So now, we’re at 11 normal dates plus 26 speed dates equal 37 dates. That’s decent progress. An introvert’s lifetime of dating experience packed into a few months.

Around the same time, Number 8 is back in town and I’m excited to see him again. Giddy excited. We went out for drinks, talked a little, made out a little, talked more, made out more. Unbeknownst to Number 8 himself, he occupied a substantial chunk of my mental space during these six months. I missed him. I wondered about his life. I fantasized about him. A lot.

He was the reason for a new rule: do not get attached to an unavailable man. Which is so obvious, I know, but it happened.

The three-years-ago Julep would have texted him every other day and stalked him online. But I didn’t want to build a story about who he was, how he was, or what he was, based on social media. The temptation was terrific, but I was curious what Number 8 would bring to the table about himself. (Ok, fine. I online stalked him one time). I found random reasons to text him about once a week, which seemed to be an acceptable, nonchalant level of contact. It was quite the meditative process to return to the task at hand, the 50 Dates Quest, with thoughts of Number 8 loitering in my psyche.

Interestingly, the next two dates were also west coasters.

Numbers 38 and 39 were both in the design field, level-headed, and mature. They loved hiking, kayaking, and all that stuff that made me go gah, yes please. It’s not like I actively sought out west coasters, but boy, I was starting to think I was on the wrong coast.

Number 40 was an Australian who was perfect on paper. He was a financial writer, well-traveled, and fluent in Japanese. Any woman would have been lucky to date him.

Dates Number 41–50 was a big blur. Three dates a week for three weeks. There was the Norwegian divorcee, the bacon mac and cheese lover, the Dominican dancer, the international law professor, the first Asian I ever dated. They ranged from small town Long Islanders to worldly businessmen. We chatted over oysters, happy hour, bone marrow, and coffee. They were all great men. Just not for me.

So here we are, November 13, 2014, six months after Date Number 1.

You would think that after the cats on a leash, after Mr. Viagara, after the Tibetan dream man, that I would have some sort of Jesus saves me moment. That the universe would see how legit my efforts were and step in with THE ONE.

Hell no. That’s not this story. Late bloomers never have it that easy. They stumble. They fall. They do everything backwards before things move forward for them.

A Few Lessons Learned

At its conclusion, I realized this was more than just a story about an introvert dating 50 men. The 50 Dates Quest was a cross-examination of my beliefs about love.

I learned to trust my snap judgements. Our adaptive unconscious, that part of our brain that flash-processes our surroundings, has great influence on our gut feelings and reactions. It was my adaptive unconscious that enabled me to read a man in the first few seconds of each date to decide whether I wanted to invest time on a second date. Learning to trust our snap judgements helps us to set early boundaries, before we start making excuses.

I learned that men are sensitive, too. Men also wrestle with feelings stereotypically associated with chick behaviors: insecurity, personal rejection, and unhealthy attachment.

I learned setting boundaries is a powerful expression of self-love. Behaviors that were negotiable in the past have no place in my life anymore.

I learned 80% of what I want in a man. And I’m working to strengthen those qualities in myself as well. He is emotionally intelligent: he understands his love language and strives to speak his partner’s love language, he has unpacked his childhood wounds, he is comfortable with expressing love through actions and words. He is worldly: he has experience living abroad or traveling, he values language and culture. He’s curious: he is self-motivated, he is inspired by nature and humans. The other 20% is negotiable.

I learned to watch and listen. People let us know early on how available they are to love; we just need to watch and listen how they show up in life. There were some great men who wanted to continue dating me and I wanted to like them back. But the one I really liked, didn’t like me back. So, I’m still trying to figure out what happens in the space between wanting love and being ready to receive love.

I learned that love is a worthwhile risk. Although “the one” hasn’t shown up (like a boss, yet), the plunge outside my comfort zone during the last six months was well worth it. I’ve expanded my vision of what’s possible and refined my ideas about love. And most importantly, I believe, unwaveringly, that I am getting closer.

I’m still 100% introvert, still a BRF authority, still endearingly, girl-Ross. And I’m still, proudly, very much the product of my Asian culture and upbringing. But now, I’m charging my own narrative with a voice that is yet again, a little stronger, a little smarter than before.


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Comments (10)

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  • Tiffany Walker- ThundaCat 2 days ago

    This is what my experience in dating is as well.. This resonates all too much!! Thank you for sharing.

  • Holly Pheni3 days ago

    This was such an awesome, entertaining read! I empathize with you fully and admire your boldness to stick to the plan and share it with us!

  • Ashley Adams10 days ago

    Best piece of writing I've read in a while! Please, please continue. I am so intrigued not only by the self inflicted challenge of your experience, but just by you in general. This piece made me want to know you and be your best friend haha. What do you do as a career, I am so curious? Someone needs to contact this woman to create a show or a movie based on this brave, self searching experience.

  • Marcia Milliner14 days ago

    I really enjoyed reading your journey, though Im in to women. I am also a introvert 75% of the time and have had my main three big heart breaks between the ages of 15-21, I have my life on track coming in my adult life and think some of your ideas would help me find a lady in my liking and if not life goes on but I can really relate. Great story again 👍🏾

  • Kundli Matching20 days ago

    Amazing story to read

  • Great story with just the right amount of humor in the situation. Best of luck with the search.

  • Bugsy Watts24 days ago

    Thank you for sharing! Your narrative voice is impeccable. Keep writing :)

  • Excellent narrative here

  • Manisha Dhalani25 days ago

    As an introvert myself (maybe not 100%), I want to say I love this so much and admire you for going through this. I must've done something similar but I never had the diligence to put it down in a reflective piece like this. I can relate to your lessons. Thanks for sharing!

  • Elysia Dawn25 days ago

    Why would anyone want to date that many men, even if they're an extrovert? I have better things to do than spend all my time meeting losers. It is more efficient to weed them all out quickly online until you find a good one. (Which is what I did. I found perfection that way too.)

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