When to Let Your Freak Flag Fly

Okay, fam, we gotta talk about when and how to “be funny” and “show the cray.” A wise man once told me that perception is stronger than reality. Nowhere on earth is this more true than in online dating land. 

Humor is a Double-Edged Sword

Scenario #1: Gentleman A is filling out his eHarmony profile. He decides it would be funny to write that he only likes women who eat celery. Woman A reads the profile, laughs, and sends a witty message to get the convo started. Woman B reads same profile, wonders if Gentleman A has a celery fetish, and blocks him forever just to be safe.


Profile Writing Tips:

  • Do remember that your potential matches do NOT know you, your cute quirky side, or your amazing sense of humor—yet.
  • Do not insult the online dating platform.
  • Do not insult your readers.

The goal of online dating is to actually meet in person. Shocking, I know. Therefore, your best bet is to remove unnecessary barriers to conversation and meet for coffee already! Yes, your profile should reflect your fun-loving nature. No, do not proclaim to the people of the internet that you can’t go to sleep without kissing your dog goodnight—save that tidbit of goodness for Date #4. Yes, I know the Plenty of Fish website is begging to be roasted in the comedic flames of Hades, but either get off the platform or leave those jokes on the table.

You might argue that anyone who doesn’t understand your humor is not a good match. But you will never know if your match would appreciate your fabulous wit if you scare them away never meet in person.

Scenario #2: Imagine you have had a terrible day at work. Now in moment of peace and quiet, you open the dating app of your choice and statements like these await your beleaguered mind:

  • “If you like shopping, good luck with your search.”
  • “I only date men who can do more pushups than me. #crossfit4eva”
  • “I only date women who can make me laugh.”
  • “If you can’t cook, move on.”

How do these statements make you feel? Laughing yet? No one wants to perceive negativity after a long day. These writers were trying to be jerks quirky, but you are tired and over it.

Test the feels from these alternatives:

  • “I’m more likely to hang out at the park than in a mall.”
  • “I love fitness and am searching for my work-out buddy :-)”
  • “Do you love to laugh? So do I!”
  • “Cooking is my favorite team sport. Will you join me in the kitchen?”

Freak Flag Timing

Have you ever given your number to a potential match only to have them turn into a crazy different person 3-5 texts into the convo? I have.

Scenario #3: Normal-looking guy asks for normal-looking girl’s phone number after multiple seemingly normal message exchanges within the dating app. Without warning or logical preamble, normal-looking guy has the brilliant idea to tell normal-looking girl that he finds “leather pants, tall leather boots, and leather jackets attractive on a girl.” Followed almost immediately by “do you want to date me?”

30 Rock-Conversation Turns

How would you respond? Since this is a #truestory moment, I can tell you exactly how I responded:

“Well, I don’t know you yet. And I don’t own any leather pants.”

Best case, this boy was trying to flirt with less than ideal content and timing. Worst case, he hides in the racks at clothing stores sniffing the leather pants to get his jollies. I will never know because he ghosted before we could meet in person. Thank goodness.

The moral to this story is keep the cray under wraps until you can meet in person and defend your uniquely brilliant and likely unflattering statements with further explanation should you see a look of horror flicker across your date’s face.

And, joke wisely, my friends.

Idol-Talented but Cray

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