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I think the biggest problem is the age difference. You're 9 years older than his 18yo little girl. That's enough to piss a father off right there. He's also your boss which is another potential problem. He may take it as a sign of disrespect while you're dating her and he'll definitely hold a grudge if/when things don't work out. It's highly unlikely that they won't work out. 18year olds are stupid as shit and you'll learn that really quick when dating one.
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“It is better to be rich and healthy than poor and sick” - Dave Barry
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