11 Awkward Moments You Can’t Avoid In Your Early 20s


1. The Career Shakedown (Inferior)

When you’re talking to an acquaintance about career/jobs, and your situation is decidedly “worse” than the other person’s.

This is highly conducive to awkward joke-making; thus, enabling the other person to silently pity you even more than they already were.

2. The Career Shakedown (Superior)

When you’re talking about career/jobs, and your situation is decidedly “better” than the other person’s.

No matter what you do or say here, you’re pretty much an arrogant douchebag.

3. The Roommate Breakup

When you and/or your college roommate of 3 years decide to ditch the postgrad dream (Tindering together on an Ikea couch) so that one of you can live with Alex from high school and pursue music more seriously.

The move is understandable, but the breakup conversation is Miles (Teller, Darius, Plumlee) worse than an actual breakup conversation.

4. The Goodbye Party Caboose

A caboose is like a member of someone’s entourage, except instead of being Filet Mignon they’re decidedly Turkey Tetrazzini.

When Trevor has that goodbye party for when he moves to San Jose, his goodbye party will inevitably produce a caboose; someone that he’s not really friends with, but is there due to friend of a friend association.

When it comes time for goodbye hugs and the like, it’s always great to observe the caboose.

5. The Amateur Hour Weekend Recap

When, during one of the first few weeks of work, you tell your co-workers what you actually did over the weekend.

Upon seeing their looks of horror, you realize your grave error. It’s a pretty big one, because you’ll then be forced to endure the “that guy” label for 9 whole months (or however long it takes until the next new hire does the same exact thing.)

6. The Overage Moment Of (Summertime) Sadness

When you’re at a house party/bar where they don’t card, and realize that you can no longer exist amongst this cadre of screaming children; that, at the moment, appears primed to overtake a handful of totalitarian regimes.

7. Social Media Stalker Knowledge

When you’re talking to someone, and they tell you something that they know you’re aware of (due to their social media post about the topic), yet act like they’re revealing that information for the first time.

This puts you in a weird spot — you don’t know them well enough to call them out on it, so you both just have to nod and accept this new reality of human sadness.

8. Coming Out Of The Career Closet

What happens when you tell your loved ones what you really want to spend your life doing.

Reactions range from very supportive, to secretly upset, to openly (and heartbreakingly) bigoted.

9. The “Leapfrog”

When you or a close friend gets a job or promotion that “leapfrogs” them ahead of the friend group. I.e., what happens if your unemployed friend finally gets a job after 8 months of searching, and that job happens to be way better than anyone else’s job.

Classifying this as awkward is undoubtedly douchey. To that, there are two responses; one, perceived superiority is secretly the purpose of 55% of all friendships. And two, an occurrence of this magnitude drastically alters friend group homeostasis; the alteration in power structure now means that Dane is at the bottom, and Dane is too sensitive to mercilessly make fun of. Nobody wins.

10. The Ma’am/Sir Bombshell

Great inflection points in life:

  • Learning how to ride a bike
  • Getting rejected by your Junior Prom date
  • Getting called ma’am or sir for the first time
  • Being 62, getting surround sound in your house, inviting all the other empty nesters to listen to the surround sound, and then not knowing how to use it.

11. The “What Are We?”

You are two humans, in a very uncomfortable situation that will soon be immortalized through a slew of furious text messages.