Tiger Woods
Another repeat sext offender, Tiger Woods's scandal streak was more impressive than his swings back in the day. Say what you will about golf being boring, but this guy was clearly not opposed to spicing things up - behind his wife's back.
Among his many steamy convos with his many mistresses, one of the most hilariously cringe-worthy attempts to get suggestive occurred when he was texting reality show contestant and cocktail waitress Jamie Grubbs:
Sir... what?!
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