Who Wants to Date a Loser?

Dear Jason Adair the Unlicensed Therapist,
I have a friend who is pressuring me (and others) to fix her brother up on dates. He seems nice but I know his story and it involves professional disgrace, financial problems and depression. None of us feels comfortable introducing this man to anyone. I've tried to put her off but she won't stop. She is blind about her brother and a real control freak. How can I get her to back off without telling her that her bro is a loser no one should date?
-Frustrated Friend

Dear Frustrated,
You have just entered into my third favorite relationship paradox; the degree of acquaintance to a person is proportional to the number of truly horrible things you know about that person. This is why it's so much easier to date a person you've just met rather than someone you've been friends with forever. The biggest problem for you, and the loser brother, is that most of the information you have about him probably comes from his sister complaining about how he used to pee on the neighbors dog, beat up homeless people, and steal medicine from the neighborhood retirement home. In all actuality though, he probably never really peed on the dog, but just said he did to sound cool. As for finding him someone to grind his professionally disgraceful loins against, I recommend fixing him up someone who has wronged you in the past and deserves to be stuck in a soul killing relationship they will never get out of because every time they try he will threaten to kill himself. If you are to nice for that kind of payback, you should try befriending some women who work for Health and Human Services and set them up with him. Not only are they trained to deal with people like that, but they're all kind of suckers for a fixer upper.

Your Friend/Holy Avenger,
Jason Adair the Unlicensed Therapist