Flirty Text Fails That Would Turn Shakespeare in His Grave theCHIVE

Flirty Text Fails That Would Turn Shakespeare in His Grave

Ty Aug 17, 2026

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Man, I was lucky.

You see, I was never much of a “flirty texter,” nor was I ever very good at it.

Luckily, we were all using BlackBerrys back then and screenshotting and sharing online wasn’t as prevalent.

‘Cuz I’d be all over this place.

My jokes never landed through texts, my pick-up lines were somehow MORE awkward in messages than in real life, and my emoji game was weak.

At least now? You can save yourself with a well-executed GIF, no?

Nonetheless, I feel bad for these flirty text fails that ended in flames.