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.


Make New Friends? Keep the Old? A Struggle Story

I find it impossible to keep in touch with people.

Mostly because when the idea occurs to me to reach out to someone and I begin to execute it, I become filled with fear that I will be texting them at the most inconvenient time, like they just had to put their dog to sleep or they’re in a job interview but forgot to silence their phone or they’re driving and will become distracted by the noise and it will lead to their fiery death or they’re still mad about that ineffectual thing I said 4 years ago.

Or even worse, we realize we don’t really have anything to say to each other, or we are afraid to say things to each other, and the exchange becomes unsure small talk and it dawns on us that we’re accomplishing nothing and that our friendship was an illusion.

Of course, that’s a completely irrational way of thinking. I enjoy when people reach out to me, despite my hatred for the question, “How are you?” Because that question opens up the emotional floodgates and causes me to reflect on all the things that I am, yet the rule-follower in me still somehow insists on replying with an unengaged, “Good.”

There’s also social media. I have yet to decide if I think this helps or hinders keeping up with friends from a distance. On the one hand, it does keep all the happenings in your friends’ lives. Recently, I realized that I will often share a piece of news about someone by saying, “My friend, so-and-so…” and then it will dawn on me that so-and-so have not actually had a conversation in several years, but I still feel connected with so-and-so because I saw the pictures from their trip to Tahiti. But is that really friendship? The constant viewing of someone else’s highlight reel?

And maybe because I’m feeling particularly sentimental, I will decide to reach out to so-and-so and say, “Hey, how was Tahiti? Love the pictures!” And they will respond with, “Hey, thanks! It was good.” And what do you do then? Where do you go from there? Is so-and-so interested in continuing this conversation or are they wondering why the hell I’m contacting them when we haven’t talked in years? And then I feel stunted and slightly embarrassed and afraid to ask about what their favorite part of the trip was, how was the food, what are their hopes, dreams, and fears, have they found personal satisfaction and happiness and if so, where did they find it? Was it in a burrito? That’s the closest I’ve ever come.

Perhaps I am on the wrong types of social media. I’m only on Twitter and Facebook. Facebook is a really good way to get a general view of what’s going with hundreds of people and Twitter is a great way to remind yourself of how funny you are. I’ve seen people having all kinds of laughs with Snapchat so maybe that’s the way to go. But how do you make new friends if you’re always looking at what your old friends are up to?

I feel like people are inherently insecure, that we all have times when we feel lonely and unimportant, and that throughout history, humans have always been searching to connect with someone, anyone, and those connections at the very least form an experience, a funny story, and at most they form a friendship. We used to keep those connections up through letters and phone calls—mediums where we feel less inclined to censor ourselves—but quality of connection has been traded in for quantity, i.e. how many “likes” your post gets. And our instinctual sense of propriety has evolved into being afraid of being vulnerable, despite our longing for connection.

This post may seem strange and because I, too, am a victim of the insecurity condition (probably way more than the average person), I am putting a disclaimer here to apologize for the strangeness (and for its reiterative nature, because seriously, who needs another social media is ruining human connection story? Says the blogger), even though this is something that I think about a lot and it certainly falls into the awkwardness category, because what is awkwardness but insecurity? And lately, any time I say, “I’m really bad at keeping in touch with friends,” the person I’m talking to almost always says, “Yeah, me too.” And yet I feel like I’m always hearing stories about what that person’s friends are up to, because they can find it online. Mind you, I have no plans to free myself of social media and make it my personal philosophy to call people frequently. I am the problem.

But a part of me has also always felt like I expect way too much when it comes to friendship. Probably because I watch too much TV. But why write friendship that way if it’s not something we secretly all crave? A topic for another day, I suppose!

The Chaser

Apologies for the absence, awkward-teers. I had forgotten how hard it is to motivate yourself to do things when you don’t have much to be accountable for. Work begets work; don’t let anyone tell you otherwise.

That, and I do often spend the week of July 31st immersing myself in Harry Potter, and I had to spend a little extra time on that this year because I needed to realign myself into the fandom after reading Harry Potter and the Cursed Child. What a magical mess that was.

Anywho, I am trying to be better about things and to get myself back on track. I doubt I will fully get there until I have a set plan and a routine again. Until then, feel free to enjoy my instability as I cry my way through Pitch Perfect 2!

Today we shall discuss The Chaser—and no, I’m not talking about whatever you grab after you take a shot of really cheap tequila (“Something else, anything else, turpentine! Does anyone have any turpentine?”). I’m talking about the guy who only wants to date you because he thinks he can’t, and then once he thinks he can, he’s done.

I really freaking hate this notion of “the chase” in dating. I just don’t understand why anyone would want to play games with people’s time and emotions. But I suppose when I see a cute fella, I’m too focused on making sure I don’t lean on the burning candle to think about whether or not I’m looking “too available.”

But back in the day, when I didn’t know any better, I gave a strange guy my phone number because he asked for it. This was the first time someone I had never seen before in my life just point-blank asked me for my phone number and I didn’t know what to do. He knew people who knew me, so I couldn’t give him the wrong phone number. And he was standing very close to me, so I panicked.

He texted me a few minutes later asking if I would meet him at a bar down the street. I said no. I was tired. And I had no interest in spending time with someone who asked for my phone number before I had even said a word to them. Of course this whole thing was all my fault because I gave him my phone number and I was answering him. Because I get no pleasure out of making things simple for myself.

He texted me again the next day, telling me he was going away for the weekend and I should hang out with him before that. I declined again. He texted me a few hours later saying, “Good news. My car is in the shop.” I said, “I’m so happy for you.” He said, “I like your sass.” That should have been red flag number one right there. He liked that I was being mean and withholding. He must have had some serious mom issues.

He asked me to hang out again. I said no.

This went on and on for over two months. Everyday, I would get another douchey text saying something along the lines of, “Are we ever gonna hang out or am I gonna have to return this engagement ring?” And other sexist things. I told him I had been a fat baby and he made fun of me for it ruthlessly.

He would ask me to hang out and I would say no.

One time he said, “You’re killing me, Smalls!” And I responded with the monologue from the s’mores scene in the Sandlot. He told me he was starting to think I was a crazy person. He called me Jill when I asked him to call me Jillian. He asked me to hang out again and I said no.

And then, one day, right around Christmas, he texted me again about hanging out. I had to work that night. He knew where I worked. And it was Christmas. And the thing is, I was lonely. I hadn’t been working at this place that long, so I didn’t really have friends there, and I was just out of college and all of those friends were scattered. These horrid text exchanges that made me roll my eyes were the only social exchanges I had; this had become my most consistent relationship.

So, I told him to come by the restaurant where I worked and we could have a drink after I was done.

He texted back that he would be there, albeit with some hesitance. I think he was already losing interest. I wasn’t sassy anymore. I was no longer a puzzle for him; granted, his method for solving the puzzle was shoving the same wrong pieces together over and over again until they were so worn down, they gave up.

So, after two months, he came and we sat down and we had that drink.

And my suspicions were confirmed. He was the worst. He called the dishwashers in the back “filthy Mexicans.” He told me he was kicked out of his frat in college for forcing two girls to drink so much, they got alcohol poisoning. He called me an idiot multiple times. And then, as he took his last swig of beer, I breathed a sigh of relief and prepared myself to tell him off, heavily considering kicking him in the shins in the process.

“Listen,” he said, before I could open my mouth, and I realized I had maybe said three collective sentences since this rendez-vous began, “You’re nice and all. That’s the problem. You’re nice. I thought you were a strong girl. But I guess now that you’ve fallen for me, you’ve gotten vulnerable.”

There were no words. Just the vapor from my boiling blood coming out my ears and skin pulling away from my bones one goosebump at a time.

“If you want to make a night of it, you can come back to my place.”

I let the rest of the vapor forcefully out of my nose like an angry bull.

“In the immortal words of Taylor Swift, never, ever, ever,” I said slowly.

“Awww, I hurt your feelings,” he rubbed my shoulder awkwardly and then he was out the door.

A part of me thinks he must have known what a horrible person he was. That’s why he wouldn’t give me the chance to really reject him. He badgers people until they will go out with him and calls it charm. He gets his rocks off from building someone up as strong and then accusing them of weakness.

There are all kinds of reasons some people are chasers. Some of them need the drama, the thrill; they live by the notion of getting the things they want. The thing is that once you have it, you will not be satisfied until you have the next thing you want, and you will get bored with the prior thing. And then there are the people who hate everything because they hate themselves the most and thus will try to make you hate yourself for reasons as stupid as being a fat baby.

How Can You Tell if a Guy Wants to Hang Out?

No, really, I’m asking.

This has always baffled me.

Maybe it has to do with the rise of texting technology. Don’t get me wrong. I love texting. Never call me again, please. With texting, I can ponder and plan out dialogue thoroughly and possibly come across as witty and charming (note very literal use of the word “possibly”). Texting is like scripting my life.

But everything has its downsides. Like many people, I sometimes have a hard time understanding if someone, particularly someone I don’t know well, is kidding through text. Add that to the fact that I already don’t pick up on subtle social cues and things get messy.

So, as these scenarios go, let’s say I am part of a budding romance (because metaphors about asexual reproduction are probably best here). We’ve hung out a few times, we’re talking a lot, it’s going well. So we’re texting, we’re smiling, texting, and lol’ing. My repartee is at an all-star level.

And then suddenly, I get something along these lines.

“You should totally come over right now.”

“You know what would be funny? If you came over.”

“I kinda miss you.”

“Why aren’t you here?”

“I wanna kiss you.”

So I put down my phone and study my surroundings. Obviously, I am doing nothing of importance. Unless you count semi-watching an episode of a TV show you’ve seen 18 times while you eat pretzels in your underwear. The only thing noteworthy thing I’m doing is talking to you…and I could easily be doing that still if we were to hone in on your suggestion and maximize it to our greatest benefit. But are you being serious? Or are you humoring me while you’ve actually got your arm around your wife? Ah, there’s the rub.

I never know how to respond to this. I have gotten it wrong on multiple occasions.

Case 1: He is actually joking.

I say, “I’m actually free right now.”

And he responds with, “Ooohhh. Yeahhhhh. I was sort of kidding.”

And then it’s awkward. What the heck do you say to that?
“Haha yeah, me too. JK. I’m really busy right now. That’s why I am responding to you so quickly. Because I’m really busy.”

Dr. Jillian will still do everything she can but unfortunately, the conversation is…terminal.

Case 2: He is not joking.

I say something along the lines of, “That would be nice.”

And, instead of him actually telling me to come over because God forbid I attract a rational human being, he just basks in the coming-over fantasy. Like, “You could help me finish this pizza.” And I say, “Mmmmm, is it meatball?” This is how I sext.

This conversation has the opposite problem. This conversation has achieved immortality.

And so we continue to discuss all the different things we could do if I went over. They are all nice and totally feasible. Then, one of two things will happen. Either we will get into 2am territory and suddenly he’ll send a terse, “Are you coming over or what?” Whoooaaa, where did that come from? No, I will not be. Nothing good can come of 2am.

Or we will continue our pleasant conversation about everything that could have absolutely happened if he had just extended an invitation and then I’ll wake up to a, “Why didn’t you come over last night?” With a sad emoji face.


I ask you, readers, how, HOW, are we supposed to know the difference between the two? Are there signs? Is this just one of the many dating things I’ll never understand?

I’m really happy with my boyfriend for many reasons. And one of them is that I don’t have to deal with this shit. We can happily text each other knowing, “These plans are your plans, these plans are my plans, from family parties to making baked clams, and if I ask you to come on over, these plans were made for you and me.”

Text Anxiety

Texting someone new is an emotionally agonizing experience. Usually when you just start texting someone, you’ve only met them once or twice, which means the foundation of your relationship thus far is probably, “You seem nice, and I’d probably bang you before I’d bang the people surrounding you.” Thus the entirety of your future relationship lies within the rectangle in your purse. The texting will prove if you are verbal matches, if you can repartee, banter, if you are compatible spellers or grammartists (not a word, but dammit it should be!). Your texts have all the power to make or break this thing, and your strategy is imperative, like a game of chess. And if that isn’t pressure, I don’t know what is.

It all starts off with the exchange (cue ominous music).

I have never asked a guy for his phone number because I never want the ball to be in my court. I was tricked once by a guy who was developing a texting app on which you could send people doodles, so he asked me to help him test the app and send him a doodle. He was unbelievably gorgeous and charming, so naturally I acquiesced. What did I send him? A poodle eating oodles of noodles. That was the best I could do. I did not send a heart or a smiley face or something flirty. I sent things that rhyme with doodle. Because I am a hopeless case. But I digress.

The exchange. So, he moves first. You are going to give him your phone number. Your real phone number. Not 10 random digits that come into your head, not your very large brother’s phone number. Your actual phone number. He should pat himself on the back for that one as it is. And then you play the waiting game.

There are some devious bastards out there who send a text right away with just their name. They make you think they are braver than you by asking for your phone number, indicating that they ain’t afraid of starting this thing goshdarnit, and then they do a cheeky flip-flop on you, leaving you nothing to work with, and the two of you are stuck in a text stalemate. Nobody wins in a text stalemate.

Then there are the guys who abide by the three day rule, because they get some kind of sick joy out of knowing that you are going absolutely crazy wondering why on earth they haven’t texted you. There are also the guys who never text you because they just like collecting numbers from people, knowing that they can text them if they feel like, because they’re big shots. It’s very easy to have a lot of friends when you don’t try to talk to any of them. Stay away from both these types. They are not worth your time (note that this is me talking to me here).

The guy who texts you as soon as he gets home might be worth a word or two, but oh dear Lord, what should those words be?

You hear your phone ping and naturally you grab it right away (I actually do not have a text tone or vibrate for this very purpose. This sort of anticipation would literally kill me). You see the unrecognizable number displayed proudly across the screen, and you open the message app to reveal: “Hey, it’s Brian. How r u?”

Oh dear, indeed. How am I? Victorious, that’s how I am. So victorious that I am going to look past his use of text abbreviations, you think as you do a little happy, jumpy shimmy. (It’s not that you’re against abbreviations, per se, it’s just that with the invention of touch screens, typing out whole words is so easy and it makes the sentences look so complete and beautifully English and it makes you, Brian, look oh so smart and careful…but you have nice pecs so…) But rather, how does Brian want me to be? Sexy? Is that a state of being one normally associates with oneself? “Hey Brian, I’m sexy.” No, that’s not right. How am I really, though? Tired? Yeah, I’m a little tired. Should I tell him that? That I am tired and exasperated by dispassionate jaywalkers? Is that hot? Are people for or against jaywalking these days? I can never keep up.

You ponder your answer for 17 minutes before you settle on something, but hey, you don’t want to appear too eager anyway.

“Hey Brian. I’m good. How are you?” Yes, that’s good. Keep it generic for now. Jaywalking opinions are solidly third date conversation. And you’ve asked him a question, you brilliant minx, you. Now he has to answer you. It would be rude text etiquette not to.

His response comes in a mere two minutes later. Brian knows Brian, Brian knows how Brian is. Sigh.

“I’m good. Last night was fun, right?”

Now, you’re feeling a bit manipulated. I mean, you did have fun, but he is sort of telling you that you had fun and also asserting that he is right all the time. Brian probably didn’t put that much thought into his semantics, but it is all in the subtext. Do you really want to be with a manipulator? What else will Brian insist is right? You’re pro puppy killing, right? Dessert is awful, right?

But…the pecs!

“Yes (or should I put, “Yeah”? Is “yeah” a bit more aggressive? A bit more laid-back, yet powerful? “Yes” might be read as, “Yes, sir,” and then that may put me in the weak spot. Ooh ooh ooh! I got it!).” Accordingly, you delete “yes” and put, “Yup. Very fun.” It wasn’t just fun, Brian, it was very fun. You don’t know everything.

But…what else? “Very fun” is not a conversation starter. It may even make it look like you are avoiding conversation. And you aren’t. Not yet.

“Yup. Very fun. Would’ve been more fun if there’d been a clown.” God, you’re smooth.




What the fuck are you supposed to do with that one?

First of all, Brian, I know you didn’t laugh out loud because it wasn’t that good of a joke, but you probably would have laughed out loud if you had made it, you cocky son of a bitch. I opened an infinite number of conversational pathways by introducing a clown character, and you write it off with a Lol. Is this really how you want us to end, Brian? I will not give you that power. You will not have the last word. You will not have the last Lol.

 Alright, you, what’s your next move?

You could ask him what he’s up to. No, you can’t, because then it might make it seem like you’re trying to hang out, and you just saw him 12 hours ago. You could expand on the clown thing, but you’d probably only be met with another Lol. What you need to do is give him something he has to engage in, something he cannot ignore. Something interesting that reveals something about you, just so he has an idea of the mess he’s getting into.

You change the channel and find that Lord of the Rings is on and that it will be followed by The Shawshank Redemption. Man is it a great day to be hungover. Ooh, that’s it! Movies! I will ask him about movies.

“Have you ever seen Lord of the Rings?” This is excellent. From here you can talk about characters, which installment is his favorite, if he read the books, how much Quenyan Elvish he knows. Oh, the possibilities!

And two hours later, you have been met with silence.

What did it mean? Was he not a fan of Peter Jackson’s interpretations? Was he out at another bar getting another girl’s number, telling her about the crazy girl from last night who had a thing for clowns? Was he dead? If he was dead, you’d have no way of knowing. The most anyone in his life would know about you is you were this chick he was trying to bang, and even if his family and friends looked through his phone, unless you were clearly labeled as The Chick I am Trying to Bang, they’d have no way of knowing the brief role you played in his life, and even then they’d still have to care enough to send along a, “Hey, just so you know, Brian’s dead” text, and you’d wander through the rest of your life occasionally wondering what happened to that Brian guy and if he did like Lord of the Rings and how he felt about jaywalking.

You try to distract yourself with the glorious movie marathon unfolding in front of you. You put on sweatpants, you reheat the pizza, and you’re just starting to think life doesn’t get any better than this anyway and Screw You, Brian, when your almighty phone pings once more.

“Lol no.”

Yeah, this isn’t gonna work. Check and no mate for you, Brian.

I have since thrown caution to the wind when it comes to texting/talking to a guy and tend to go full throttle with my weirdness and candor. I am luckily blessed with a boyfriend whom I can text at any time of day about a variety of subjects, from ram gagging to building forts out of cake to raps about the dangers of drugs, and he will listen to me rant about jaywalkers (if there is a car coming, you run! Run, you whackjob! That car is so much bigger than you). But boy, have I been there. And if you have never experienced text anxiety, I want to know who built you.