The Dating Game

When I was a young girl, I was convinced that one day, I would fall in love. There was

no question in the matter. It was a fact. A truth of life evident from every movie and TV show I

entertained myself with. I started off with Disney princess movies. My favorite was Sleeping

Beauty for a while, and then it was Beauty and the Beast. I’d watch these and then play make-

believe, pretending I was a princess being rescued and wooed by a handsome prince. Then came

Disney Channel shows where the quirky, dorky girl gets noticed by the cute boy. I fell in love

with Teddy and Spencer from Good Luck Charlie and I watched hopefully as Alex from Wizards

of Waverly Place found love. When I was becoming too old for Disney Channel shows, I became

obsessed with the love story of Riley and Lucas in Girl Meets World. I was a pre-teen, on the

cusp of adolescence, and I watched their scenes over and over with a deep longing for a boy to

love me like he loved her. Looking back, that was the moment the yearning began. I had rooted

for Teddy, Spencer, and Alex, but when I saw Riley and Lucas (slightly embarrassing, I know),

that’s when it clicked. I saw myself in the position of those girls being loved by those boys. And

I wanted it.

As I left childhood and entered young adulthood, my parents showed me romantic

comedies. They became my first true loves. Instantly, I fell in love with their predictable plot

lines, common tropes, witty dialogues, and interesting scenarios. They were a comfort. A warm

blanket wrapped around my shoulders. A hot chocolate or a chai latte warming me from the

inside out. A hot shower at the end of a cold day. These movies became a part of me. At my very

core, I became a hopeless romantic. I looked for love everywhere. I thought of it on long car

rides, on the bus, on the train, on flights, long walks, and before I drifted off to bed. My days

were overtaken by daydreams and fake scenarios I'd play out in my head. Boys I thought were

cute who would profess their love for me. Celebrity crushes I’d run into and fall madly in love

with. Adventure and heroism and action were not of interest to me. Love and care and human

connection were.

I remember thinking about when I would have my first relationship. I remember, because

I thought about it all the time. I knew my first relationship wouldn’t be the person I married. I

wasn’t naive. What I didn’t know was how hard it would be to even find someone to love. It’s

draining, trying to convince others to want and love you. It’s hard to find guys who live up to

heightened expectations that come with being single for so long. In my favorite movies, the guys

are all perfect: attractive, kind, funny, smart. They’re charismatic, making both the main

character and the audience swoon. They’re perfectly imperfect. Rough and disheveled but soft

and gentle. Grumpy and serious but oddly protective. Arrogant and annoying but secretly soft.

Energetic and friendly, but secretly wounded. They’re the good and the bad, but they’re not bad

men. They’re complicated, wonderful, lovable men. They’re men that give you hope, men that

make the world seem a little less scary and make you feel a little more...optimistic. And the way

they love the main character is so beautiful and soft, the audience begins to desperately wish the

same could happen to them.

Now that I’m inching closer and closer to no longer being on my parent’s health insurance, I’m

realizing that life is not so simple. Sure, these rom com leading men and women

face hardships. Things happen in their lives that bear resemblance to the difficult world we’re

trying to escape. But the love, the feelings, the pursuit, that part is easy. The pain of dating isn’t

shown. And if it is, it ends in a happily ever after. I’m not saying I’ve gone completely cynical. I

haven’t given up completely on the idea of a happily ever after. I still do have hope. I do believe

that dating can be painful and there can be a light at the end of the tunnel. What I’m saying is

that I thought I would have my first boyfriend in high school, and that never happened. Oh well,

better to focus on my friends and myself anyway. I went to college and I knew that, surely, it

would happen there. I got slightly closer but, still, no. I graduated and moved to the city and got

my first “big girl job.” Nothing. It even got worse: the dating game started. I began with such

fresh and blinding hope. I knew it would happen, so it didn’t matter if it didn’t happen right then

and there. But, over time, I was burned. The longer it takes and the older you get, you form a

jagged wall around your heart. You start to lose hope in dating. You definitely lose your faith in

men. Of course, there were reasons I stayed single that were totally up to me. But isn’t that a part

of the problem still? Sure, I wasn’t completely undesirable. Sure, some men were interested and

wanted to date me or, at the very least, sleep with me. Instead, it was me who didn’t want to date

them. But, the thing is, my entire life I’ve dreamed of love. I’ve fallen into mad crushes and built

close friendships with skills that are completely transferable to forming and maintaining

romantic relationships. And yet, I remain single. Either unable to be liked or unable to like back.

Unable to get past a certain point. Always turning up with another failure to add to my

collection.

So, eventually, I guess I did become cynical and pessimistic. I started to believe that

maybe love wasn’t for me. Some people are meant to fall in love, they do it as easily as learning

to walk. Others are meant for other things – even as I write this, I know that’s not true. Everyone

is built for love. Everyone is meant for love. Romantic love, yes, but also all kinds of love. And

yet I cannot shed the cynical, doomsday feeling that maybe love isn’t in the cards for me. I could

possibly learn to embrace that with time. Realize that the life I have built for myself, my

friendships, my family, my activities, and hobbies, will have to be enough for me. They will

have to be my big love story. But that would be easier said than done. Because there is still a

black hole in my stomach full of loneliness and desire and yearning that is growing larger each

day. One day, if nothing comes of this, I think it might eat me alive.

Which leads me to where I am right now. On a date. Date number 1,000. Well, not really,

but it sure feels like it. He’s talking to me, telling me about himself, and I’m feigning interest.

Nodding and smiling and interjecting with ‘that’s so cool!’ and ‘that’s so fun!’ My outfit is cute,

but not legendary. After so many dates, I’ve started to lose the urge to create an amazing first

impression. I’ll find a cute outfit and put on makeup and make my hair look nice. But I won’t kill

myself trying to look perfect. Nine times out of ten, nothing comes from these dates. We’ll never

see each other again. It would be a waste.

“So, tell me about yourself. Where are you from?”

I refocus my eyes. I’ve been staring at him but not looking at him, which, if I were more

hopeful, would make me embarrassed. I nod and adjust my smile. I prepare to recite the standard

script. I swallow the lump down my throat. It’s showtime.

“Well, I’m from the suburbs. I’m an only child, so I grew up with my parents. We’re

really close, I love them a lot. Since I don’t have siblings, my friendships are really important to

me. I have some really close friends from high school and college who are more like family to

me. I went to Loyola and moved back home after graduation, but now I’m back in the city! I

really love it here.” My voice tilts with enthusiasm. I feel nothing of the sort. Instead, I wait for

what I will say that will sabotage this date. What answer will make him lose interest. Or, more

likely, what will make me lose interest and long to be back home on my couch in sweats

watching TV.

He nods, smiles. He seems interested. So it wasn’t that. I wonder if he’s going through

the same thing I am right now. Overanalyzing our interactions, playing the game; The thing that

makes dating completely impersonal and cold and nothing like the romantic comedies I grew up

on. Maybe he’s also waiting for the moment when it becomes abundantly clear that we will

never hear from the other again. Maybe he can even feel my pessimism from across the table.

Maybe it’s infiltrating him as well. Instead of admitting that, he says, “That’s really nice! It’s so

nice you have a good relationship with your parents.”

“Yeah, I love them,” I say, smiling. What else do I say here? Describe a time when my

parents and I did something fun? What are the rules on talking about your parents and your

family on a date? It’s probably frowned upon. I’ll leave this where it’s already at.

“What do you like to do, like, hobbies-wise?”

What do I like to do, like, hobbies-wise? The thing about dating is that it takes up so

much of your time. Or, at least, the way I date takes up so much of my time. I’ve never been

good at balancing relationships. I’ve always loved intensely. Without a romantic relationship,

friendships became my everything. My self-worth became intertwined with them, and most of

my time was spent on being with others rather than being by myself. It’s what’s happening now,

with dating; I’m completely consumed by my desire not to die alone. I guess old habits die hard.

I have to think about what I used to like to do, before I went on date after date and had to recover

on my off days.

“I like to hang out with friends, do yoga, read, write... I’m really crafty, so I like to

journal and knit and draw. That kinda stuff. I love TV and movies too, I’m, like, an OG iPad

baby.”

He chuckles at this, a sign of approval. I know deep down that I’m fun, but listing off

these hobbies doesn’t make me sound like the best time in the world. I’m not a 23 year-old with

a hyperactive social life. At my core, I have the behaviors of a 40-year-old woman. “I sound like

an old lady, I know.”

“Well, I think it sounds fun, what you like to do,” he says, smiling at me. I search in his

eyes to see if he really means that, or if it’s just one of those things you say on a first date. From

what I can tell, he seems to mean it. But, who am I to say? I’m usually wrong about these things.

“What do you like to do?”

He goes on about his interests, how he’s not much of a reader except for some Stephen

King novels (typical). How he loves movies, especially horror movies (absolutely not). How he

likes to hang out with friends and go out to get drinks (I can get on board with that). How he

loves to travel (yes, yes, yes). That he enjoys playing video games in his free time (alright). I nod

and smile and show interest, just as he did for me. And, really, we do have things in common.

I’m not completely feigning interest. But my heart isn’t in it.

I’ve had dates before where I’ve known then and there that this is a person I could like.

It’s a normal first date, nothing extraordinary, but the feelings are different. When he talks about

himself, I’m fully paying attention. Not thinking about what I’m going to order or what I’m

going to do when I get home, or how much longer until I can leave. I’m genuinely laughing and

smiling and trying my hardest to flirt – an unnatural thing for me – so that he knows that I am,

genuinely, interested in him. As we continue to talk, I don’t realize how long we’ve actually

been on this date for, and I hope that we can make it last a little longer. It’s not magical

butterflies or love at first sight. I don’t think he’s the one immediately. But there are little signs

that let me know that this is someone to invest some more time into. This is someone to see

again.

Unfortunately, I’m not having these feelings right now. I’m having a good time. It could

be a lot worse – it has been a lot worse. But I don’t feel...invested. Excited. Any of the magnetic

pulls or sparks or giddiness that come from a great first date. As he continues telling me about

himself, I can tell there’s no spark. Nothing is really reaching out to me and asking me to grab

on. He’s a very nice person, and we will have a decent date, say goodbye, and never go out

again. He will become a stranger I once went out on a date with. Maybe his dating profile will

live in the graveyard of my past messages, or maybe he’ll unmatch with me. Who knows.

Whenever this happens – and by ‘this’ I mean my lack of interest – I tend to wonder if

there’s something wrong with me. I know I’m a beautiful woman and kind and smart, and

anyone would be lucky to have me. Blah, blah, blah, etc. etc. I mean, something might be wrong

with me internally. Maybe there’s something broken in me that doesn’t allow me to easily like

someone. It’s stumped me, because I’ve always been a romantic. You would think that I would

go on these dates and become infatuated with most of them. It’s all I did in high school, fall

madly in love with boys I never spoke to. You’d think actually speaking to them would cause an

unrelenting crush. Instead, there’s only been a select few that I’ve really liked. Only a few who

I’ve really wanted. Maybe the longer I’m single, the more picky I am about who I have a real

crush on. Or maybe, my capacity to love has changed. Dry and dusty from lack of use, maybe

it’s slowly capsizing in on itself and its walls are getting closer and closer together. It’s

discouraging, really. To feel as if it’s a fight to like someone. It’s no longer just about the

rejection from men. That hurts too, and it never gets easier. But it’s also about the frustration

with myself when I can’t even get there. It always hurts, seeing someone ready to offer me

everything I’ve wanted, but not being able to accept it. Maybe there’s something wrong with my

wiring.

After two hours, our date comes to a close. He has to go home and get some stuff done

before tomorrow. I have to too. He pays, we stand up, and we walk out of the restaurant. It’s not

too late, still early enough to have an evening to myself when I get home. He waits with me

while I order an Uber, and we talk in the meantime.

“I had a great time,” he says.

I smile, looking up at him. He seems to mean it. “I did too.”

“Maybe we can get together another time soon? Get a drink or something?”

I nod and force my lips into a polite smile. “I would love that.”

Before our silence can become awkward, my Uber approaches the curb.

“Well, that’s me. I’ll text you! Thank you again,” I say, giving him a hug goodbye.

He returns the hug before releasing me and giving me one more smile for the road. “Get

home safe!”

And with that I turn on my heel, check the license plate, and slide into the Uber. I let out

the longest of breaths, not realizing I was holding it, and my heart starts to beat at a normal pace

again. My stomach starts to untwist itself. I begin to relax.

I’ll probably never see that man again. In a day or two, one of us will either break it off or

we’ll let it fizzle so that no one has to be the “bad guy.” He’ll move onto the next and so will I.

And the next, and the next, and the next, until I’m “fixed”. Until I finally find someone who can

bring to life the hopeless romantic in me. In the meantime, the game will start over for me and

he, most likely, will find someone. I’ll wonder if I’m the last stop before these men find the loves

of their lives. If I’m meant to go on date after date, leading these men to realize they want to

settle down, and allowing them to find their dream partner. I’ll tell myself it’s a coincidence and

that’s just how dating works. And then I’ll go back to the apps and swipe as if my life depends

on it. Maybe I’ll find a guy who I think I like, whose kisses give me butterflies, and who I begin

to picture a future with. And then maybe he’ll like me, but most likely he’ll ghost me. Or tell me

he’s not ready for anything serious. And I’ll either give up or give in to the modern day

“situationship.” Who knows, really. It’s a loop I’ve been on for what feels like ages, and I just

want it to stop. I just want to fall in love. And be loved. To understand what it is everybody’s

raving about. To be pulled from the claws of cynicism and into the light of optimism and hope. I

want to be an annoyingly in love person. One of “those couples.” And even though we had a nice

time, now that the date is over, I just feel sad. I know I’m right back where I was before the date

started. Nothing has changed.

I lean my head on the car window and close my eyes for a moment. Before I know it,

we’ll be back at my apartment. I’ll get ready, take a shower and change into comfy clothes. I’ll

complete my extensive skincare routine, maybe even add in a face mask, to feel luxurious. I’ll

clean or do laundry or watch something on TV. I’ll enjoy my own company and pretend as if

that’s enough for me. I’ll make sure I don’t wallow and instead, find ways to be happy with

myself for the evening. But deep down, I’ll ache. I’ll feel it, somewhere in my bones. My heart

will tug. I’ll feel this slight sadness that could be all-consuming if I turned my attention onto it.

And when I get into bed that night, I’ll go back to swiping on the apps in a meaningless,

mindless, zombie-like trance. And then I’ll wake up and do it all again. The endless, relentless,

dating game.