My Top 5 Most Awkward Halloweens

I had a lovely post all written out for today, perfectly catered to reflect my awkwardness, and then my work computer crashed and I was told the files were not recoverable. So, alas, here we are. It was important to me to get a post out today since I missed last week, so I guess I’ll just have to wing it.

Halloween has always been such a weird time for me. You’d think it would be my favorite holiday, as it combines two of my favorite activities: being overly theatrical and soliciting candy from strangers. But for whatever reason, Halloween always leaves me with a particular, profound sort of emptiness. Maybe it has never lived up to my expectations. Or maybe I just associate it with less than fond memories.

I’m really looking forward to the weekend ahead of me: I’ll spend time with friends I haven’t seen in a while, I’ll get to sleep next to my boyfriend, I am entirely too proud of my costume. But I have no doubt I will still feel weird and moody and uncomfortable and somehow lonely. Because that is what Halloween does to me.

Anyhow, here are some of my awkward Halloween memories to share with you.

The Time I Thought I Turned My Dog into a Pumpkin

The first Halloween I have committed to memory is when I was three years old. I was dressed as a fairy princess and was upset that I wasn’t accomplishing real magic, despite having a magic wand in my possession. My father, bless his heart, convinced me that if I closed my eyes very tightly, I could turn my dog, Brittany, into a pumpkin. While my eyes were shut, my father very swiftly put Brittany into another room and put a pumpkin in her place. I opened my eyes and my jaw dropped to the floor, but my reaction was not what my father was hoping for. I became grossly upset with myself, worried that my dog was gone for good, that she was trapped in a pumpkin and terrified, and that I had used my powers for evil. Of course, my dog did come back, but I retired my wand that day, and a part of me thinks that the reason I’m so obsessed with dogs is my penance for trapping my dog inside a pumpkin. And my punishment is that they usually ignore me, for I need their love way more than they need mine.

The Time I Learned a Lesson About Society

When I was five or so, I really wanted to be Belle for Halloween. She had brown hair, brown eyes, and liked stories, so we were essentially twins. My mom, at the time, told me that all Halloween stores were out of the costume, but I knew the truth when I saw my skinny cousin wearing the costume a few weeks later: they didn’t make the costume in my size. Chubby girls couldn’t be Belle. I will believe in progress when I see a movie with an overweight woman as a romantic lead, and not a single comment is made about her weight. Dear world, promote health, promote happiness, and stop making women feel like shit about themselves all the time and then telling them their insecurity is unattractive. You’re unattractive, world.

The Time That Somehow, Every Single Year, I Managed to be Either the Only Kid in School Who Wore a Costume, or the Only Kid in School Who Didn’t


The Time I Went Trick-or-Treating by Myself

Up until the eighth grade, I only really had one close friend, and we went trick-or-treating together every year. But one year, in the fifth grade, she had pneumonia and couldn’t go. I had two options: I could mooch off of my brothers’ candy, or I could go by myself. Destiny’s Child was big at the time, and so naturally I valued myself as a strong, independent woman, because Beyonce told me to, so I went by myself. I’m not sure if there is a sadder sight than a 10-year-old going door to door, her mom waiting for her at the curb, with her head hung in defeat because she realized this was incredibly boring, miserably asking, “Trick-or-treat?” in her voice that is 50 years ahead of her body, development wise. This is the first time I can recall having the weird Halloween feelings; feelings of overwhelming loneliness that are evoked by the sights and smells of Halloween to this very day.

The Time I Had Alcohol

My first alcohol experience was on Halloween. I had approximately four sips of Kahlua, so naturally I felt wasted. I ended the night eating an entire bag of Oreos and watching Donnie Darko.

So, combine a dog’s soul forever encased inside a vegetable, the denial of my royalty due to unfair discrimination against kids who love to eat, a slew of memories of getting it wrong, a lone trick-or-treating, and the mind-fuck that is Donnie Darko, and you get one awkward time of year.


All the Things That Made Me Cry This Week

  • A video game about two brothers who search for a spring filled with magical water that will heal their father of his illness. I would like to note that there were several things in this video game that made me cry, up to and including a giant turtle getting reunited with her children and a couple of rams that just looked really happy to be alive.
  • Four dead possums.
  • Every dog I saw.
  • Especially my dog, because he is the best dog.
  • A particularly graphic scene in a book about animal torture.
  • That there will come a time when I will never see all the people I know again.
  • That I’m not living up to my potential.
  • That I am living up to my potential.
  • “Just the Way You Are” by Billy Joel.
  • “Do You Believe in Magic?” by The Lovin’ Spoonful.
  • Because I missed my boyfriend.
  • Because there is so much hate and violence in the world.
  • The hero-worshipping of Ken Bone.
  • Bees are dying.
  • An article about a man who made his wife a real-life Harry Potter pensieve as a wedding gift.
  • That I never got to say goodbye to my cat (who died 9 years ago).
  • I have zero confidence in my performance at work and thus I am questioning all of the choices I’ve made over the past few months.
  • Because I finished my lunch.
  • Trump bumper stickers.

An Open Letter to the Boy I Thought Had Ruined My Life

Recently, I found a letter I had written to a boy I dated about five years ago. He had just broken up with me, and I had never been more devastated. I walked around my college campus in zombie-like state, with puffy, red, wet eyes for days. I couldn’t sleep. I couldn’t eat. I thought I had lost the love of my life and there was no coming back from the pain. I think the letter may have served as a cathartic means to get all of the bad feelings out, but man, is it a doozie.

The thing is I was essentially thanking him for breaking my heart. Not in a self-empowered, I’m-better-off way, but, like, thanking him for his time. Thanking him for stooping so low as to spend three months in a relationship with me. Thanking him for “loving me.” I talk about enclosed gifts that I don’t remember buying, but I’m pretty sure I also never sent them. In the past, I’ve had a habit of buying gifts for the guys who dump me. I’m not sure what I’ve meant by them. Maybe it was a reward, maybe it was a, “See, look how great I can be! You sure are missing out.” No matter what, the gift had a whispered undertone of, “I have low self-esteem.”

They were usually pretty nice gifts, though. Don’t tell my boyfriend.

It’s kind of funny because I remember the breakup itself and the post-breakup madness pretty well. I even vaguely remember writing the letter. But I don’t really remember anything about him.

I remember his name, what he looked like, a couple of the things we did together. I have one vivid memory of him drunkenly screaming at a picture of Kel Mitchell and then throwing up everywhere. And the dick pics. Oh, the dick pics. He had a real affinity for those. A calling. A passion. I was too young and inexperienced at the time to question it, though I remember not being particularly fond of them. To me, they all had the personality of a student athlete who is having trouble balancing his schoolwork, love life, and his sport. And when he really can’t handle the pressure, he has to yell, “Believe in yourself!” into the mirror over and over through his tears.

I do not remember what we talked about or what we had in common or why I liked him so much. As I squeegee all my brain folds, I cannot, for the life of me, recall an attractive quality about this individual, the great thing that separated him from all of the other ones who had dumped me. The letter does not mention anything like that either. It’s a thank-you note mixed with elegant pleading, embalmed in nonsense that I’m sure I thought sounded poetic at the time.

He broke up with me over the phone, while I was sitting in my car. He’d actually made the official breakup statement while I was on my way to the car, but I waited until I was comfortably seated inside to scream every profanity I knew. (The conversation actually ended with him saying, “You’re making me feel really bad. I’m going to have to hang up.”)

Here are the various reasons he gave to me as to why he wanted to end things: 1) He wanted to be able to fraternize with the fairer sex to his heart’s content while he was on vacation. Enjoy the herpes, buddy. 2) I was neither “spunky” nor “athletic” enough for his liking. I’m not sure what he meant by spunky but I have a feeling in his mind, it was a girl who enjoys unsolicited pictures of male genitalia. As for the athletic thing, well, we played tennis together once, so obviously this was extremely important. Oddly enough, this is not the first time a suitor has been surprised by my lack of athleticism. I don’t understand it, and if you saw what a struggle it is for me to walk three steps in a straight line without falling, you wouldn’t understand either. 3) I had gained weight.

And so on.

Essentially, I was given a laundry list of all the things about me that were unattractive. I guess it’s nice that he put so much thought into it. You can see why I missed him so much.

Then the words, “I just don’t think you’re good enough for me,” came out.

And I think that’s what did it, in the midst of all this ridiculousness. This one phrase. This phrase that ate away at my psyche. The phrase that put me in therapy. Because this pet rock of a human being thought I didn’t deserve love. And I believed it. That much was clear. The letter said that, the gifts said that. And that was the way I felt, for a very long time.

So, it is rather exhilarating to look back at this letter and laugh so hard, think, “Oh God, I said that? I thought that?” To shake my head at how stupid I was five years ago, as I attempt to reflect on why I thought this was a problem worthy of a second thought.

And it is perhaps even more exhilarating to write this letter…

Dear Boy Who I Thought Ruined My Life,

Who are you, again?

Best, Jillian

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!