“Jaw With John” – Jack & Jill Went Up The Hill And Jill Kicked Him In The Nuts And Stole His Money And Ran Away, Possibly

My friend “Jack” recently got engaged to “Jill.” Jack and I have been friends literally since before we could walk.

Jill is 26, and this will be her third marriage. Both previous marriages ended with her having affairs. She also has a history of doing drugs and stealing. She has stolen from me, my family and Jack’s family. She has stolen medication, money, you name it.

Jack insists that she is “doing better,” that she has recovered from her mistakes and would never do things like that now. Jill has never apologized for her actions and blames everything she did on her previous husbands.

I worry for Jack but he brushes off my concerns. Jill has made it clear she won’t let me be around Jack unless I allow her to be present. Recently she has started mocking and insulting me.

Should I keep trying to express my worries that this will only end in tears for my friend, or should I back off, let him do as he wants and prepare to help him clean up the mess? — Worried and Wounded

Dear Worried:

You know what they say: Third time’s a charm!

Jack is a Grown Ass Man. He can handle himself juuuuuuuust fine. As for Jill, time will tell if she has learned the error of her ways or if she is just a sociopathic leech. You need to step back and let Jack figure this one out on his own. If he gets burned, then so be it.

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