
According to reports, the mystery woman is an exec at Morgan Stanley in NYC -- so girl obviously has experience hitting the mother lode.
As for the boat -- "Captain Jack" was not at the helm ... we hope.

perhaps a friend, why you guys jump to conclusions, and even though his girlfriend which is the problem let him live in peace
I bet they are friends and what a nice boat and time of year to use it! Crisp and cool and gorgeous days. I really love her doggie! Pugs rule! She's darling.
Didn't he learn from the last way to young for him wife. Marry him cheat on him and get a bunch of his money. Billy is an old man and he really needs to look for someone closer to his age. I think Betty White is single.
any chick that wears the headband thingy is like just out of highschool. She should wear her hair in a chignon instead.
he cant be so stupid to think this chick loves him ..he is like her grandfather...billy joel was relevant in the 80's..dude find a woman you have something in common with(geritol,viagra,arthritus medicine,depends)someone you can share thoughts with...not some girl that you can only paw at and molest... you dirty old man
Maybe she's right for him, but I hope he's careful. He should do what Paul McCartney did this time around. Find an "uptown girl" who loves him and fits into his life instead of a floozy who's always looking for an upgrade.
IF HE WAS WORKING AT KMART.....SHE WOULDN'T BE W/ HIM!!!!
LOOKS LIKE SHE COULD BE HIS DAUGHTERS FRIEND
why is he wearing a helmet?noone else is
I bet that young asistant is banging her behind his back
hey @ midnight toker: the helmet is 'cuz he rode his motorcycle and he had "Movin' Out" playin' on the stereo....
I agree he probably needs someone his own age to make it work.
But he has $$$ so (he thinks) he wants/needs some young chick. Men his age like/want to feel young, that is why they pick on young ones, if they can!!
Regardless, I hope it works out for him.
It seems true, unconditonal long lasting love is the one thing he has always wanted and has always escaped him, even with all his success. Sad! Granted alcoholism probably plays a role, but still sad, nonethless!!! :-(
Britney Spears might miss a lot more 'X Factor' auditions ... because she can! Simon Cowell gave Brit damn near free reign in order to sign the pop star to that $15 million deal -- but is it backfiring? We'll tell you what peeps on the set are saying.Plus, Chris Jericho's…