Flirting is like gambling -- the odds are stacked against you, you should never do it while drunk, and it'll more than likely crush your soul into smithereens. But that didn't stop these 16 people who flirted hard and came up empty-handed:

1. Landing a pickup line is a challenge all in itself.

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ileikpie

2. Never flirt with a tired person.

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inspiredot

3. Just because you can rearrange a person's name into another word, doesn't mean you should.

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4. No digits because she saw yours :/

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runt-of-the-web

5. Brutal, but literally true.

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6. Some say this man has never flirted again.

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