My Top 3 Most Awkward First Date Moments

I’m a bit of a perfectionist.

Dating was important to me from a fairly young age, because I thought that being in love would fix all of my problems, from my glaring emotional insecurities to why pants never fit me right. So when the time came around for me to date, I wanted to do it correctly.

The problem was that I was growing up during the dawn of the internet and a golden age of romantic comedies, and while young me hoped this would provide answers, it only created a crowded and ambiguous thought bubble full of questions. Questions that I still have to this very day.

And so, here we are.

1.


From my pre-teen years onward, I always thought it was kind of weird that men were expected to pay for everything on dates, based on what I had observed and read. I understood where the idea came from, but now that we were living in a time in which women earned their own money and forged their own independent paths, it didn’t make sense to me. I also feel horribly uncomfortable whenever anyone does anything for me. If I ever broke my leg, I would still limp my way to the kitchen for a glass of water to avoid inconveniencing anyone.

Of course as an uptight, angry teen, I thought the idea of a woman paying was highly progressive and that my cause would contribute to the betterment of humanity. To the point that I was pretty militant about it. Any guy who offered to pay got a hard no (it, of course, never occurred to me that the money I spent usually came from my father’s wallet since I had no pennies to speak of at the time).

When I was about 19, I was talking to an ex-boyfriend and he casually mentioned that while he supported my viewpoint, if someone wants to treat you, sometimes it’s polite to just let them treat you. So when another guy pulled up to my house for our first date, saying he was going to treat me to miniature golf, I decided I was going to try and be treated. What could be so bad about a treat?

When we arrived at the mini golf course, I started to panic. The idea of letting him pay made me feel so…dependent, powerless, weak. I was coming around to understanding that’s not always how the treat-er sees it, but the helplessness that started to take over my body was uncomfortable and making me feel sick. So when he was about to walk over to pay for our mini golf outing, I knew it was going to happen.

But that didn’t mean I had to see it happen.

“I…uh….” I stammered.

“You okay?”

“Yeah, all good, I just uh…” Think, Jillian, think! What is a good excuse? His beautiful face is staring, waiting.

“I’m just…gonna stand over here.” Yes, that makes sense.

“What?”

“I’m just gonna stand over here for a minute.”

“Do you need me to…stay with you?”

“No! No…that’s alright. You go over there. I’m just gonna stay here.”

He raised one eyebrow at me, but he did listen. And he did date me for a little while after this. Bless him.

I then proceeded to hide behind the bathroom building and let the transaction happen at a distance.

It occurs to me all these years later that I could have just said I had to go to the bathroom. That’s probably a more normal thing to do, right? Oh, well.

2.


Because I, like many, was a walking bucket of contradictions (still am, just different contradictions), even though I felt I was pursuing a great feminist plight financially, I also still really wanted boys to like me. This combined with a total lack of social and self-awareness at the time really made some weird science happen.

I used to be a lot more preoccupied with physical appearance than I am now. I think being healthy and feeling your best is important, but back in my teenage years, my warped brain was downright obsessed with keeping my weight low and making sure nobody knew that I ate.

Which proved tough. Because I can eat, friends. Like, really eat. I have no sense of fullness. Only a sense of sickness and self-loathing.

But I thought that showing off this talent would be unattractive to the opposite sex. This started to be a sort of problem when I entered the “getting asked to dinner” phase.

Once for a first date, a guy took me to a nice pub with a small menu, mostly consisting of burgers, wings, and other messy foods that I could chew loudly and get all over myself as I licked the plate clean. Also, he had already said he insisted on paying, and if I was going to allow that, you could bet your arse I was going to get something real cheap. I perused the menu for something that would make me seem dainty and low-maintenance (even though I am neither). I settled on a stuffed mushroom appetizer, knowing how impressed he’d be by my teensy appetite.

“Are you sure that’s what you want for your meal?” The waiter asked. “It’s kind of small.”

“Oh, yes, that sounds perfect,” I responded as my stomach growled at me.

“You girls always eat like birds,” my date said through a small smile (see! It wasn’t just me! We all had them fooled).

Turns out “kind of small” meant one mushroom, stuffed with breadcrumbs and cheese, in the middle of a white plate.

Now I didn’t want to eat too quickly and appear gluttonous or make him feel like he had to eat his actual, normal meal quickly, so I decided to cut the mushroom into crumb-size pieces, fit for the delicate birdie-ness I was emanating, and ate them at a very slow, calculated pace. I think I actually finished after he did.

Then I went home and made myself nachos and he never called me again.

3.


This story, while awkward, is also about effective techniques one can adopt in the face of douchery. It is about survival.

I went on a first date and it was going well. Pretty low-pressure stuff: fruit smoothies, a walk around town. He seemed nice.

Of course it turned out, for this man, a date that’s going well means he’s totes gonna get laid after.

So, as we pulled into my driveway, I leaned in to give him a tame kiss on the lips, and he took my face in his hands and forced my mouth open with his tongue. I pulled myself away because, ew, gross.

“What are you doing?”

“You, hopefully,” he responded with a smugness so potent, I wanted to throw acid on it.

He started leaning in again. His face was mere centimeters from mine.

“I’M OVULATING!”

“What?”

Then I jumped out of the car and ran.

Advertisements

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s