Bosses represent a wealth of awkward opportunities, right at your fingertips. I once had a slightly intimidating boss who really knew how to bring out the discomfort in me. Every time we’d speak, I’d leave the conversation with a damp upper lip, a racing heartbeat, and another awkward story to tell. Case in point (people, take notes): I was working in retail, and the boss in question is a coveted designer. While working on the sales floor, he approached me and asked who was selling the most. “Allegra,” I responded, thinking he was asking me which sales associate was selling the most. “What’s Mallegro?” he asked me. “Ummmm, Allegra?” I repeated hesitantly. “No,” he said, “I mean which DESIGNER is selling the most.”
The takeaway: Clarity. Make sure that when you’re talking to you boss, clarity is always lacking.
2. If Sweaty Sleeper, Have A One-Night Stand
Hey, do you guys sweat a lot in your sleep? No? Well I do. And, to be honest, waking up to my boyfriend asking me if I peed on him is something I could get used to. Something I’m wary of? Having a one-night stand. I have a hard time believing I’d be as comfortable waking up in my pool of sweat next to a stranger. Moving my stringy, sweaty hair aside to say “g’mornin!”
3. Perform An Untimely Sing-Along
So, you’re with a group of friends, a Frank Ocean song comes on, and you’re all like, “OMG I love this song!!” You’re bobbing your head to the intro and then—BANG—you go in for the first verse, “A tornado flew around…,” except, it’s 5 seconds too soon. You try to play it cool, but there’s no use. Everyone heard you, remember? There were no actual vocals to drown out your voice?
4. Pull A “Fashionably Late” Entrance At The Wrong Time
I can never show up at a party at the right time. When everyone shows up late, I’m already there, going on hour three, and spilling my fourth glass of vodka sprite on my head. Annoying? Certainly. But awkward? Nah. Awkward is showing up “fashionably” late to a party that turns out to be more of an intimate, sit-down-dinner affair. Do that, and get high before.
5. Watch Sex Scene With Parent(s)
They key here is timing. Timing, timing, timing. Because you could EASILY walk in on them watching Seinfeld, and then what good would that do? But if you time it correctly, you’ll walk into the TV room and plop down on the couch next to your dad as soon as the James Bond girl mounts Pierce Brosnan to the tune of seductive elevator music. You freeze. You can’t leave. And so you stay. And watch.
6. Open Your Eyes While Kissing
Ideally this will be with someone you don’t know too well, or perhaps don’t know at all! First kisses aren’t always the prettiest, which is why people tend to keep their eyes closed. Ergo, keep your eyes OPEN and you will secure at least one awkward eye-lock.
7. Be A Low Talker
Coined by Seinfeld, a low talker is someone who speaks at a barely audible volume. Again, this will diminish clarity from any conversation and it’ll also give you an air of unparalleled awkwardness. Just imagine a low talker at the altar. Or a low-talking debater. The list goes on.
8. Zone Out
Another crucial facet to leading a socially awkward lifestyle is having that rare ability to zone out at the drop of a hat. For instance, I don’t think any one random person could doze off in the middle of a one-on-one conversation with their Rabbi. I, on the other hand, can. And such a knack—while admirable—has also gotten me into some sticky situations. Situations that you’ll hopefully find yourself in if you listen closely.
Take a conversation—any conversation, really—and just zone the F out. Then, when you come to, nod feverishly like you know exactly what’s being said and you couldn’t agree more. If they ask you a follow-up question like, “But what if he didn’t fire the chef? How will I explain that?” you attempt a bullshit answer, and trail off into a faint mumble.
9. Snot Bubbles
Just make ‘em happen.
10. Be A Perennial Target For All Types Of Balls
(Except the scrotum kind.) Be that girl (or guy) whose head seems to have a magnetic attraction to softballs, basketballs, baseballs, kickballs, and the like. A quick and public smack to the head (or nose, or cheek, or neck) is a foolproof way of turning a comfy situation into an awkward one.
11. Awkward Pause
I for one regard an awkward pause as a crippling sense of discomfort that, with every passing second, plunges you deeper and deeper into an unspeaking mess. But not everyone agrees. Jerry Seinfeld, for instance, loves a good awkward pause. For him, it represents the perfect moment to make your move on a girl (“Anyway, like I was saying, I couldn’t make the transition from conversation to sex. There were no awkward pauses – I need an awkward pause.” – Jerry Seinfeld) And so, to ensure that your pause is as unbearable as possible, make sure all of the weight of the conversation is on you. For instance, a therapist session. No one has the power to break those awkward pauses but yourself.
Perhaps you’ll wake up mid-sleepwalk as pure gibberish is spilling out of your mouth to your roommate. Or perhaps you’re the adventurous type of sleepwalker who ventures outside and exposes her weird, zombie-like habit to the world. Maybe you’re on vacation, and when you come-to it’s 4am and you’re three miles from your bungalow, incessantly ringing a stranger’s doorbell—who knows! Either way, you’ll wake up feeling awkward.
13. Try Your Hand At Flirting After Long Hiatus
In a perfect world, you’ll have just come out of a long-term relationship. But, as we all don’t live in a perfect world, you could also have just re-emerged from a 2-year-long, self-inflicted hibernation. Regardless, you’ll be unseasoned, unprepared, and will thus use something like this for your first pick-up line, “Hey, is it just me or did somebody fart???!”
14. De-Robe Tight Sweater In Public
Maybe you’re at the office, maybe you’re on the subway, or maybe you just got a tad flushed during a job interview. Casually, you attempt to take off your sweater, until your head gets stuck in a sleeve, perhaps the constraint of the tight wool on your head causes you to salivate uncontrollably, and the situation is no longer casual, but dire and irreversibly awkward.