The Top 5 Most Awkward First Texts I’ve Received from Gentlemen Callers

Guys, I understand all too well that there’s a certain amount of pressure when it comes to starting a conversation, especially with someone you’re trying to impress.

But…come on.

-“have fun last night”

It honestly took me several hours to realize this was a question. As I went about my daily tasks, I kept wondering what it could have meant. Was it some sort of H.D.-inspired commentary on how superfluous words can be? Are you telling me you left your fun somewhere last night and you think I have it? It seriously took everything I had to realize it wasn’t just four random words. Does that make me thick? Probably. But because I didn’t understand, I did not respond. What are the three rules of texting? Punctuation, punctuation, punctuation.

Hey I got your number from your coworker. It’s your favorite customer from tonight ;).

Ah, but that’s my secret, random dude: I hated all my customers.

This was from my bartending days. I never did forgive that coworker. Also, just my two cents, be very careful with your winky faces. A relationship must get to a certain level before incorporating the winky face. A premature winky face could easily be read as, “I’m outside your window with binoculars and a gag.”

Hey QT got any nudes?

I can only assume he was looking for Quentin Tarantino and had the wrong number. Granted, I am not promoting harassing Quentin Tarantino for nude photos of himself or anyone. It’s just the only way I can justify anyone sending me something so gross.

So, you be Goose and I’ll be Maverick? 😉

…this is just extremely confusing on multiple levels. Oy with the winky faces already!

Quick, who is your favorite Pokémon?

Had he picked literally any other fandom, this might have led to at least a greater conversation…but, call me a cynic, I had a weird feeling about where “Pokémon” would go.

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Being THAT Person

Here’s the thing about archetypes: they spring from truth.

I’m not particularly good at a lot of things. I’m not athletic, I’m not musical, I’m not artistic, and I have no charisma. These are the realities of life and I’m okay with it.

But when you’re young and you’re desperately searching for your place and purpose within the world, as if those things exist so simply, when you’re walking around blindfolded and swinging a stick around, looking for a piñata filled with passion, chances are you’re just gonna focus on the first thing you hit.

And my first hit was the English language.

I’m a nerd. That much is certain. But I’m not the cool kind of nerd (i.e. the ones who grow up to make a lot of money, and it turns out, the whole time, if you’d just taken off their glasses, you would’ve realized they were good-looking the whole time). I’m a word nerd. A grammar nerd. I have fiercely strong opinions about hyphens, apostrophes, and em dashes—opinions that could be summed up with the statement, “They should be used properly.”

Don’t get me wrong. I’m all about individual creative style. Huck Finn is my favorite book, and you can’t act like there aren’t any conventional violations in that text. Style serves a grand storytelling purpose and for that reason, it deserves utmost respect.

It took a very long time for me to get used to colloquial speech. I guess I grew up thinking that people wanted to be corrected: that my interrupting them mid-sentence to say, “You mean Mary and I,” was extremely helpful and educational, and they would walk away thinking, Not only is Jillian a considerate and charitable friend, she is also so polished and intelligent. Mary and I. Who knew?

I did realize, embarrassingly late, that they were more likely thinking, Bitch.

I remember the first time it occurred to me that I might be a bit uptight. It occurred to me because I went to a party and this person I kind of knew said, “I’m surprised to see you at a party. You usually seem pretty uptight.” Then he walked away and left me to reflect.

And the conclusion I came to was that I didn’t want to be THAT person. The person who, in the year 2008, every teenage boy came up to and said, “Why so serious?” (RIP Heath Ledger). The person who couldn’t physically handle ending a sentence with a preposition. So I set out to make some changes. As history has pointed out, you can be happy or you can be right.

It’s amazing how much actually working in the book business helped with this goal. It made me realize that while people can do their very best with quality control, no one is infallible. A book contains a lot of words and thus a lot of ways to screw them up. And while I thought I knew a lot about this language we call English, I really was ridiculously ignorant.

Then, one day, one of my interns told me she was going to write a letter to a publishing company about a typo she found in one of their books (an irrelevant typo. Not an unfortunately funny, context-changing one like public policy vs. pubic policy). My response?

“C’mon. Don’t be THAT person.”

While calling someone out for being the exact THAT person I used to be could be construed as hypocritical and bitchy, I saw this as more of an important transformative moment. Like God was moving me into the “Maybe” pile.

Here’s the thing about old habits: they run deep.

While I can’t recall a time I have outright corrected anybody in the recent past, I can say that I have made it clear that I value pristine written communication in the workplace. At work the other day, one of my colleagues got a load of my Interview Dos and Don’ts board.

She said, “Can you fix this board? ‘Dos’ should be apostrophized.”

I said, “No, I don’t believe it should be. An apostrophe indicates possession or omission of a letter. In this case, ‘Dos’ is plural, not possessive.”

“Well, thank you for the grammar lesson,” she deadpanned.

When I went home later that night, my father asked me about my work day.

“Oh, you know, just had a chat with my coworker about proper apostrophe usage.”

My brother overheard and rolled his eyes.

“Congratulations, Jill. You’re THAT person.”