THE BEST OF ASK IVANA ADVICE FOR THE MILLENNIUM

FOR 14 years, Ivana Trump shared her worldly wisdom with GLOBE readers delivering no-nonsense advice on love, business, and family matters.

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Here are some of the straight-shooting socialite's greatest bits of guidance from her fan-favorite Ask Ivana column!

SHOULD I DATE MY SON'S FRIEND?

Q I'm a 42-year-old woman who got divorced seven months ago. I have a son in college who recently brought home a friend for a weekend. This boy is a very handsome 21-year old, and ever since the visit he's been phoning me almost daily to chat and he says he wants to start dating me! I know it's trendy now for women to have younger boyfriends, but I still feel weird about it. And I worry it may affect my relationship with my son. What should I do?

- R.R., RENO, NEV.

A Usually, I'm all for a younger man-older woman A relationship, but this isn't some random toyboy you met at a party. This is one of those boundaries that shouldn't be crossed because it could create an extremely awkward situation for your son. How do you think you'd feel if your mother was sleeping with your buddy? Go ahead and feel flattered, but listen to your inner warning bells, and don't encourage the relationship.

I CAUGHT CHEATING MY BOSS ON HIS WIFE ?