16 Of The Most Excruciatingly Awkward Text Conversations We’ve Ever Read

It’s no secret that people tend to be significantly bolder over text than in person or even on the phone. Still, knowing this, we never cease to be amazed at the gall some people have when they’re hiding behind a keyboard.

From Tinder trolls to random weirdos, the following conversations are utterly mortifying and just downright awkward. Get ready to cringe.

1. The world’s most uncomfortable game of 21 questions.

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2. Not everyone’s great with rejection.

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3. A wildly inappropriate, yet ambitious request.

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4. Nice save there, bro.

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5. A very bitter date.

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6. Proof that persistence never pays off.

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7. This romantic proposal:

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8. Just stop.

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9. Creepy Mc Creepington on the prowl.

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10. This uncomfortable role-playing scenario.

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Emily Burns

Written by Emily Burns

Writer and editorial specialist based out of Austin, TX.