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Ok I guess....

1. I was born wealthy but blew it all

2. I can't sing worth a darn

3. I am not good at this game.
Thanks for all the guesses.
I was planning on waiting for fiesty to guess before I reveal since I got hers correctly.

If she doesn't reply in the next 30 minutes or so I will reveal.

This will let me try the multi quote feature
 
The TV series “That 70’s Show” had a character that used the phrase “I’m going to put a boot up your ass” or “I’m going to kick you so hard you’ll be wearing your ass for a hat”. While I’d heard the saying “ass hat” for years (it’s a common label in the Army) I had never heard it on TV until then.
 
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