Why Dating is Juuuuuuuuuuuust The Worst

My boyfriend of ~a year and friend of 3+ and I broke up about 2 months ago. Rather than going with my instincts and deciding to be happily alone for the rest of ever, I, like many in my generation who are busy and/or passive and/or desperately wanting to give up but can’t for fear of ACTUALLY being alone forever or missing out on what is presented as a quintessential life thing-y, decided to join OK Cupid. This is also basically my first foray into dating not-friends that I haven’t known for a year already.

First of all, that name. OK Cupid? I mean, c’mon, can we get a little sadder? I don’t want an ‘okay’ cupid, I want a fucking fantastic cupid. I want a cupid who knows me in and out and knows my shortcomings and can match me up with the yin to my yang. OK Cupid makes it sound like I got assigned to a disgruntled Cupid employee who half-asses his job. I mean, I get it, I half-ass my job on occasion, but when it comes to long-term lovey-dovey bullshit, I want someone who knows and cares about what they’re doing.

I’ve talked to several dudes (yes, I say dudes, this is probably part of what makes me awesome/single), went out for one first date that made me question every life decision I’ve made that has led me to this sad, pathetic point in my life, and generally had a better than expected, non-murder-y time. In fact, even though by the end of the date I wanted nothing more than to take off my pants and sit on my couch alone with a bottle of wine and some spicy Thai food (WHICH I TOTALLY DID AFTER THE DATE, even though I wasn’t hungry. What, who are you to judge my fatty-fat eating habits?), I’ve agreed to go out with him again. The chemistry or whatever wasn’t exactly there, but I take a while to warm up to anyone. And, because I hate myself, I already have two more first dates coming up in the next week. So here’s the insights about myself and dating I’ve gleamed since dipping my toe back into the murky, expansive sea of tired, bored, mildly depressed fish:

1: I, as a non-feminine female who spends more money on Jimmy John’s than clothes, have NOTHING to wear to a first date.

Seriously, what do I wear? What do normal girls wear on first dates, dresses? Skirts? Fuck all that noise, I’m not setting that as a precedent/shaving! So pants it is, but what ‘cute’ top do I have that goes with pants? Like most men, my wardrobe is almost entirely plain colored t-shirts. I think I found a tank top and a cardigan, and called it good. And by ‘called it good’ I mean I totally forgot about accessorizing with a necklace/earrings and wore the only ‘cute’ flats I own that every guy I ever date will see a million times.

This is right, right? This feels natural.

3: How much makeup is the correct amount of makeup?

There’s a spectrum here, people. From naked face (no, not the correct amount) to probably-gunna-hang-on-the-street-corner-after-this-date face. Do I use this weird tube of foundation I’ve never touched to cover up my imperfections, or show my mid-twenties acne off like a real woman? And what about hair? I only ever do one thing, so I guess I better go low expectations on that. IS THIS THE RIGHT AMOUNT OF MAKEUP?! IS THIS RIGHT?!?!

2: Doing -literally- anything a human being does makes me feel awkward and judged and oh my god everyone in this restaurant knows I’m an idiot.

“What’s the proper way to cut things? How big of bites can I take? How fast should I eat? Should I be a lady and not eat all my food even though I totally could and would under any other circumstance? Does he think I’m eating all wrong? Ugh, I’m left-handed and we’re sitting on the wrong sides of each other and I keep accidentally jabbing him with my elbow and when do I get to take a bite? Maybe I’ll ask him a non-yes/no question and quickly shove this bite of food in my mouth that’s been sitting on my fork for the past two minutes while he answers. God, the waiter needs to bring me more water so I can continue sipping at it just for something to do to alleviate the awkwardness of sitting here and talking to a complete stranger.”

21 Phases Of A First Date Fail

3: Dating profiles set *everyone* up for disappointment.

No one sets out to create a dating profile that really, truly, accurately reflects them. If we did, mine would read something like ‘My name is Jessah, my wardrobe consists mostly of dude clothes, my purse usually contains a sandwich and whiskey because you never know, and my favorite part of every day is the part where I’m not wearing pants.’ Dating profiles are the first dates BEFORE first dates–everyone’s trying to put their best foot forward in what they say and how they present themselves on filling it out. I mean, I do it, too, sorta. No one is going to put a picture up of themselves that they don’t think is ‘good’. So, be prepared for every person you actually meet in person to be an uglier version of who you thought they were. What leaves me really REALLY unimpressed by a profile is grammatical errors. How hard is it to run that shit through a spellcheck?! If you KNOW you’re not great at language skills, give yourself all the help you can to not look like a moron. Maybe it’s just me that really cares, but if I can’t derive the content of your profile due to the number of grammatical and spelling errors, that’s a damn good indication we’re just hashtagNOTMeantToBe. Also if you use hashtags in your profile like a 15 year old girl who just discovered the internet…no. Just no.

4: If you thought saying ‘hello’ was gunna be awkward, just wait ’til you have to say ‘goodbye’.

I’m pretty sure the only part of a first date that’s more awkward than the beginning or the middle is the end. How do you end a date? How?! You have to stand around talking for like, another 10 minutes by the person’s car pretending to laugh at each other’s jokes before it can actually just be over. And the whole time is an internal panic–oh god, is he going to try to kiss me? I so don’t want to be kissed, we just met. Do I give him a hug or a handshake? It has to be more physical-y than how we started the date, right? What form of the word ‘bye’ should I use? How do I let him know this was fun but that I literally never want to go through this again, but that’s got nothing to do with him?

5: The date in review–a postmortem.

After said date, if you’re me and it didn’t totally bomb, you have to pick apart various aspects of it for future potential–how did conversation go? How fake was I being when I laughed at his jokes? Did I genuinely find him funny? How fast did the time pass (the answer is always ‘never fast enough’)? Personality-wise, would we get along? I mean, like, will he get to know how shitty I actually am and appreciate my dark, cynical sense of humor? Could he potentially be someone that I could tell all my inner thoughts on all human beings to (which are generally not nice things), and not write me off/actually enjoy it? Or is he just too nice of a person?

6: If you have to put calendar reminders in your phone to remember you have a date, you’re probably not stoked on dating.

I wish I had something more clever to say on that point, but I don’t. This is my life. This is what I have to do to avoid being the dick that blows people off. Zack, I’ve got you scheduled for 7 on Friday, Greg, you’re in there for coffee on Sunday at 2, Andrew, DUDE HURRY UP AND GIVE ME A TIME AND PLACE SO I DON’T FORGET I HAVE TO PRETEND TO BE A PERSON NEXT WEDNESDAY AFTER WORK.

So, in conclusion, every date ever I think will just remind me that I shouldn’t be dating. That dating is hard and feels more like a job than my actual job. It reminds me how much I LOVE just going home, taking off my pants, and chilling on the couch while eating shitty food, watching shitty tv, and playing video games. I’m just…awful at dating. Maybe someday some good looking, nerdy, semi-fit, tall, thick-haired, sexually confident, capable of shit-giving, rich programmer dude who loves his family and puppies and Netflix will find that to be an endearing quality in me. But until then, I guess I’ll keep trying, or not trying, and scheduling first dates, or not. I don’t know. But I’ll be pretty happy when this next week of dates is over because I’m assuming they’ll all go terribly.


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