When you date a proper gentlemen who truly seems to be head-over-heels in love with you, him cheating on you is probably the last thing on your mind. But that’s exactly what these sweet-looking men did to the women they supposedly adore.

1. Tiger Woods

Tiger Woods had everything a man could dream of: a career he loved, incredible success in that career, more money than most people on the planet dream of and a stunning wife who loved him. Everyone adored him and wish they could have even a fraction of his luck or skill.

Then Woods went and ruined it all in a single stroke, when the world discovered he had cheated on his wife with almost 20 different women. His marriage ended and his career took a significant knock.

2. Bill Clinton

When Clinton became president, most of us rejoiced. Unlike his predecessor, he actually seemed like a nice, dependable guy. Then that thing happened with Monica Lewinsky and he went from hero to joke in one fell swoop.

3. Eric Benet

The singer had a great career and a woman every man on Earth wanted: Halle Berry. But he apparently saw her as only a conquest, because he cheated on her and even landed in rehab for having a sex addiction.

4. Tony Parker

Parker was dating Desperate Housewives’ Eva Longoria, and they seemed like a great fit for each other. Then Longoria filed for divorce after three years of marriage.

She revealed that Parker had been frequently flirting with other women–he’d sent hundreds of texts them. And worse, he’d actually slept with one of them: the wife of his former teammate.

5. Hugh Grant

In the 90s, Grant was one of the most adorable actors in the world. But success in his career made him dissatisfied with his boo, Elizabeth Hurley.

In 1995, he solicited prostitutes and got busted. Hurley stood by his side, but Grant never really reformed, so they officially broke up in 2000.

6. Brad Pitt

Pitt was the kind of guy who could do no wrong. And his relationship with Friends star Jennifer Aniston seemed rock solid.

Then he met Angelina Jolie when acting in “Mr. & Mrs. Smith” and decided to cheat on Aniston. He’s stood by Jolie since then, but what if all that changes if he falls in love with someone else on the set of his next film?

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