Playing With Matches: Feeling the Burn of New York's Online Dating Scene

By Dylan Fitzpatrick

A humorous memoir about online dating in New York City, from a man's point of view.

• Language: English
• Publisher: BookBaby
• Release date: Mar 1, 2014
• ISBN: 9781483521688

Book preview

Chapter 1: The Importance of Being Hydrated

Fresh from a workout, I stepped out of my local NY Sports Club and into a perfect evening. New York City is easily one of the greatest places to be in the spring. As the temperatures rise and the city begins to thaw, New Yorkers lighten up. For the city’s tourists, that means people won’t respond to a friendly Hello as if you just said, Go fuck yourself. NYC is full of assholes, so it’s nice to see them warm up with the weather.

In the summer and the months approaching, Thursday nights are excellent. The nightlife is vibrant and everyone is getting a jump start on the weekend. To make matters better, the women are dressing more skimpily and doing their best to minimize their ass size as bikini season approaches.

I was pleased with life as I left the gym that night. I had just lost a much needed ten pounds so I, too, could look my best for swimsuit weather. I needed to impress the ladies as much as they needed to impress me. Before heading home, I stopped by the local Duane Reade drug store to pick up some toilet paper. As I walked in I caught a glimpse of my reflection. I looked as if someone dipped me in the East River. For the good of the public, I decided I would make this a quicker than usual shopping experience. When I walked through the door, a beautiful brunette turned and looked at me with a smile that stopped me dead in my tracks. I was like the stereotypical guy in a movie who drops what he’s holding when he sees an unbelievably gorgeous woman. If I had been wearing sunglasses, I would have pushed them down the bridge of my nose to see her better. This woman was a natural beauty, the kind that other girls hate because she doesn’t need to wear makeup. She had a flawless body and was probably the type who eats burgers and drinks milkshakes and wonders, Where does it all go?! I made a note to myself to take another peek at this Jennifer Connelly lookalike before I left.

"But she was smiling at me, wasn’t she?" I said to myself as I headed down the escalator.

I have a tendency to overthink things, and this situation wasn’t any different. I have these little arguments with myself. I try to play things cool, like The Fonz from Happy Days, but what usually emerges to the public is more like a less cool version of Woody Allen. So my internal argument began:

ME: She might dig you, man.

VOICE OF REASON: Right. A smoking-hot girl like that wants you. Especially now—fresh from the gym and covered in sweat.

ME: Stranger things have happened. This is New York, and I am in pretty good shape these days, if I do say so myself.

VOICE OF REASON: Easy, Hercules. You ran two miles and can’t bench-press your own body weight.

ME: I’m just saying, I look better than usual.

VOICE OF REASON: You still look like you. Keep in mind: A) She hasn’t seen you before, so she has no frame of reference, and B) We’re not grading on a curve. Just because your midsection doesn’t look like a bagel for once doesn’t mean you have this locked up.

ME: Touché.

VOICE OF REASON: She smiled because she’s probably friendly, and believe me, she’d probably prefer a simultaneous Pap smear and mammogram to spending time with the likes of you.

ME: OK, here’s what I’ll do: I’ll finish my shopping, and if she’s still there when I check out, I’ll talk to her.

VOICE OF REASON: Sensible.

I headed upstairs to pay for my goods and see my future ex-wife. As I rode the escalator, my inner voice chimed in:

VOICE OF REASON: Don’t be a dick.

ME: What does that mean?

VOICE OF REASON: Exactly what I’m telling you.

ME: I’m just going to be myself.

VOICE OF REASON: That’s what I meant by not being a dick.

ME: Shut up! I’m getting closer, and there she is! She’s at the top of the escalator, and she’s smiling at me again!

VOICE OF REASON: Easy. Don’t piss yourself. Pretend to be cool. Or at least as cool as anyone can be covered in sweat.

ME: OK, but if I try too hard she’ll know I’m full of shit.

VOICE OF REASON: She already knows you’re full of shit.

ME: How?

VOICE OF REASON: You’re carrying an eight-pack of toilet paper.

ME: Fuck! That is a lot of toilet paper. Why can’t they come in smaller packs? She’s going to think I spend all day in the bathroom.

VOICE OF REASON: Tell her you were planning on mummifying yourself tonight.

ME: Shut up! There she is!

As I got to the top, the woman said, Hi! She had the sweetest voice and, as I said, was drop-dead gorgeous, but more than that, she had the rare ability to make me feel like I was the only guy in the store.

I gave her a devilish smile that would have made Sean Connery himself blush, and responded, Hi. I’m a natural, if you haven’t gathered by now.

Looks like you got a solid workout there.

Yeah, I’m a little gross right now. I have to go home and burn my clothes.

She chuckled kindly at my weak humor. I’m Sonia.

I introduced myself and then, to my surprise, the conversation shifted gracefully into a friendly banter between two young strangers. Who knew where this would lead? Luckily I remain grounded at all times and never let my imagination get the better of me.

I envisioned us going out that very evening. We’d have drinks and maybe even a late dinner. We would get tipsy and discover we were perfectly compatible. I would make her laugh with silly stories but still manage to show my seriously ambitious yet artsy side (which doesn’t really exist). She would tell me intimate details about her life and show a bit of her goofy personality by doing a solo dance routine to Michael Jackson’s Thriller at a bar where no one else was dancing. We’d end up back at her place, where we would have a nice, long seventh-grade make-out session on her couch. She’d stop me from going all the way because she’s not like that. From there we would develop a highly compatible relationship—both intellectually and sexually. We’d spend days playing tennis, hitting the beach, and maybe even riding a tandem bicycle through Central Park. OK, maybe not the bike part. We’d spend evenings at home watching movies or getting slowly drunk at outdoor cafes before returning home to have some borderlinedeviant sex. Eventually we would get a one-bedroom apartment on the Upper East Side and a Jack Russell terrier. We’d name him Gus. She and I would vacation at exotic locations. Sonia just loves the Amalfi Coast. I prefer Croatia, but she would insist. You know Sonia…

After all, this woman did smile at me and tell me her name.

The conversation continued, and we started discussing some of our favorite bars and restaurants in the city, and she kept gazing at me like there was no one else on the planet. I noticed that she didn’t have an engagement ring on her finger. Did I mention she was gorgeous? I decided that if things kept going in this direction, I would ask for her number and then skip home like some love-struck high schooler counting down the two-day grace period to call her up and ask her out.

Then Sonia asked me about my workout. I told her I keep it pretty basic. The voice in my head spoke up:

VOICE OF REASON: Don’t push it and act all macho.

ME: I’m not. I’m just answering her question.

VOICE OF REASON: Yeah, but I know you. You’re going to find a way to shoehorn in a tidbit about yourself to impress her.

ME: Fuck off. I’m playing it right. I’m just going to ask her out and see if we can meet for drinks.

VOICE OF REASON: Drinks are a great idea. Drink martinis again. It always goes well for you when you’re tuned up on vodka. Remember when you—

ME: Yeah, I remember. I’ll take it easy with the booze. Just pipe down.

VOICE OF REASON: Just stick to beer this time so you don’t look like Boris Yeltsin on New Year’s Eve again.

Sonia continued, I know when I work out, I try and run through the Park. Do you hang out in the park?

Yeah, I said. I love Sheep’s Meadow when the weather’s nice.

Oh, great! Then I’ll know where to find you after my daily run.

Cool!

Yeah, I go there a lot.

Cool!

My inner voice stepped in and told me, You should probably buy a thesaurus. This was going a whole lot better than I had expected, despite my questionable command on basic vocabulary. I was doing my best not to look like some star-struck amateur while waiting for exactly the right moment to ask for her number.

Sonia continued, And after a workout, I can get so dehydrated.

I agreed, as I was likely to agree with anything she said at that point.

You know what I always stick to after a workout to stay hydrated?

No. What? The suspense was killing me.

VitaCoco! She said this enthusiastically while holding up a sample bottle of her marketing tool. I had been so busy looking at her finger for engagement rings and yes, at her ass, that I hadn’t noticed the VitaCoco logo on her shirt.

Do you like coconut? she asked brightly.

Momentarily stunned by the realization that I had been flirting with a marketer, I blurted out, I hate it. It’s true. I’ve hated coconut since birth.

Oh, she said sadly. Then you probably won’t—

I’ll take three, I said.

But I thought you didn’t like coconut.

As I said, I’ll take three.

She gave me an awkward, OOOKAAAAYYYYY… and I was on my way with my three bottles of cutting-edge hydration product.

There went my evening. I decided I should buy a few pints of chocolate chip cookie dough ice cream and light some candles when I got home. Then I’d put on some sweatpants and console myself to the soothing tones of Sarah McLachlan, the only one who could empathize with an injury of this proportion. More aptly, I felt like Charlton Heston at the end of Planet of the Apes when he discovers that his world has, in fact, been destroyed since the very beginning of the movie. Still, I couldn’t help but seeing that this was not only frustrating but hilarious as well. I was sure I’d laugh once I was through rocking back and forth with my knees to my chest in the corner of my apartment.

Heading out the door, I saw a man in his late 20s walking into the store, apparently coming from a run in Central Park. As he entered, I heard an angelic voice over my shoulder give an enthusiastic, Hi! Poor bastard, I thought.

On my way home, I tried to cheer myself up, but it didn’t work. I’d rather have Sonia leaving my apartment the following morning with bite marks on her ass. Something had to be done. This was New York City. It was full of beautiful, single women. Not all of them were electrolyte saleswomen who messed with guys, giving them false hope and driving them to drink—alcohol I mean, not VitaCoco. But where would I find these women? I didn’t know, but knew I had to find out.

Chapter 2: Playing with Matches

With my sights set on the ultimate combination of looks and personality, I turned to the most natural and organic guide I could find—my computer. I had heard about online dating and definitely had my reservations. They ranged from the possibility of only meeting desperate, lonely people ready to attach themselves to the first willing, warm body they could find, to facing ridicule from friends for having to use the computer to get a girl. Setting my hesitations aside, however, I went for it and dove into the world of the online dating site Match.com.

After downing two bottles of VitaCoco, fully hydrated but choking on the combination of coconut and embarrassment, I sat at my computer and put together a relatively simple profile. Then I did some searching and searching and searching. Soon after logging on, I realized that I had a pretty specific woman in mind. I couldn’t quite see her face, and in general I wouldn’t say that I have a specific type. The woman of my dreams is pretty simple or overwhelmingly complex—depending on how you look at it. I don’t care if she’s a cocktail waitress or an executive vice president at Goldman Sachs—I can be won over either way. Without question, a woman’s confidence can increase her overall appeal, regardless of her career. Of course, physical attraction has to be there at some level, but that can come from many things—the shape of her body, what she communicates with her eyes, her smile, how she carries herself. For me, that’s where it begins. Women are works of art, period. That’s a fact, not an opinion. The female form has been the subject of the majority of paintings and sculptures since the beginning of time. Even gay artists can’t deny women’s aesthetic appeal. They may like dudes sexually, but can’t resist the female form when it comes to their art. Think about what you hear on the radio and you’ll notice that most music is about trying or failing to get a hold of a woman. So there was nothing novel about my wishes for my dream girl. I was just hoping there’d be more to her than met the eye.

Profiles in Courage:

The first thing I learned when I joined Match.com is that all members have to create an online profile to sum themselves up for potential mates. It didn’t take me much time searching through the various profiles of single women to see that these profiles tend to follow a certain pattern, and after a while, they began to all look the same. Soon, reading a new profile became sort of like re-watching a favorite movie: You know what’s coming but you can’t pull yourself away. I have the same affection for these profiles as I do when I watch Ferris Bueller’s Day Off. I know what’s coming, yet I’m overjoyed every time Ferris pretends to be Abe Froman, the Sausage King of Chicago.

Single women who use online dating services tend to represent themselves in a very specific manner. You could take all the profiles on Match.com and use them to create the perfect model of a generic online woman dater. Let’s call her Amy. We’ll start the first place everyone starts when browsing through profiles on a dating site: With the photos.

Photos:

Without fail, Amy will include a photo of herself as a bridesmaid at a friend’s wedding. When this photo was taken, she had spent the morning at the salon getting her hair and makeup professionally done—and