7 Awkward Online Dating Scenarios You Failed To Consider

Love it, hate it, or feel meh about online dating, if you play the game, you may find yourself in some awkward scenarios you failed to consider. And when I say game, I mean “Magic: The Gathering”. Say for instance, that you meet someone online who just happens to be a blogger. When you go on a date with The Blogger, you reveal your status as the world champion of “Magic.” I suppose you had considered that The Blogger may write about the experience. But not in an completely crappy, privacy-busting way, mentioning your first and last name for all the world wide web to gawk at. My apologies to the man who found himself in this awkward scenario. Just for the record, Jon and I were born in the same town in the same year. I know this because his date also posted his Wikipedia page. Hey, I’ll bet our parents know each other! But I digress. After the jump, some more weird situations you might find yourself in if you dare to date online.

  1. Having your friend discover the online dating profile of the guy you thought you were exclusively dating. This is embarrassing because it means you are way more invested than he is. It’s even worse if he asked your friend out. That means he’s probably asking lots of girls out. Who knew a simple click of the mouse could make you feel like such an a**hole?
  2. Meeting your friend’s new boyfriend and recognizing him from his online profile. Do you act like you’re meeting him for the first time? Do you smile, nod, and ask questions? Do you pretend not to know when he tells you he has a dog? I mean, his handle is DOGLOVR74. Do you remind him about the three un-returned messages he sent saying, “We seem to have a lot in common. We should get a drink sometime”? It’s a hard call.
  3. Seeing your boss’ profile online in your “suggested matches.” You are not two years old. You understand the principles of peek-a-boo. If you saw him, than he saw you. That’s gonna make things weird. Forever and always, when he asks you to do something you will mutter under your breath, “Sure thing LongNStrong4U.”
  4. Seeing that one of your matches happens to be a guy your mom dated. And that he winked at you! First of all, how on earth is the online dating compatibility calculator thingy giving you the same matches as your mom? As your THAT much alike? You must be, since this guy clearly is unable to resist your gene pool, regardless of the decades separating you and mom in age. That is what our own Amelia concluded when this very awkward experience happened to her. She not only did not return the wink, but deleted her online dating account entirely.
  5. Getting an online message from your ex. You know when you get that email via [Insert Online Dating Site Here] and get all excited to see who sent it because it’s super long! And looks like someone actually put some thought into the virtual wooing of you! And then you discover it’s from the boyfriend you broke up with two years ago. Yeah, that’s a letdown. Also, why didn’t he just use your gmail account?
  6. Getting messaged by the guy that just dumped your friend. Your friend calls you in tears. The man she’s been dating just dumped her saying that “he didn’t feel that bliss.” Minutes later you receive a message from Bliss_Seeker1980. Surprise! It’s him and he doesn’t know you and his ex are besties. Now what?
  7. Accidentally asking out a guy on one site that had already turned you down on another. You were only trying to “diversify your portfolio” by spreading your profile around and you made a mistake. You hit send before you realized that he is the same guy from [Insert Online Dating Site Here]. He probably got a haircut or shaved off his mustache and you didn’t recognize him. Whatever the reason, you now have to brace yourself for the humiliation of being rejected twice by the same person. That sucks.

Want to contact the writer of this post? {encode=”amelia@thefrisky.com” title=”Email her”}!

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