Carolyn Hax: Friend won’t play matchmaker for ‘loser’ brother

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Carolyn Hax is gone. The following is from May 7, 2008.

Carolyn: I have a friend who pressures me (and others) to set up her brother on dates. He seems nice, but I know his story, and it involves professional shame, financial problems and depression. None of us feel comfortable introducing this man to anyone. I’ve tried to put her off, but she won’t stop. She is blind to her brother and a real control freak. How can I get her to back off without telling her her brother is a loser no one should date?

This reads like an advice columnist’s philosophy exam: “Who is in worse shape: the loser, the myopic control freak sister who defends him, or the person who befriends the myopic control freak sister but still clearly dislikes her?”

Forget it. Rhetorical test only.

Of course, if this man is corrupt, you cannot play matchmaker. Finished.

But shame, debt and depression are three Ds that leave room for recovery. Must everyone who is brought down, even by their own bad behavior, be condemned to remain low for life? Are you really as comfortable as your letter suggests?

Maybe this dishonored brother hasn’t done the hard work to fill the holes he dug, or you’re not close enough to know. Fair enough. Even if he was fully redeemed and restored to health, you would still be under no obligation to repair him, or anyone else, for that matter.

But you didn’t mention this guy’s current condition, only his past. That alone makes a case for showing this family some compassion, even if you say no.

You: “Sorry, but I don’t want to set up someone I don’t know well, not even your brother.” Repeat as needed.

She: “Why not? He is [insert sisterly rationale here].” Or: “Come on, you’re so [guilt trip here].”

You: “My answer is final.” Repeat as needed. It’s Control Freak Handling 101: the gentle but steadfast no.

Carolyn: What kind of person thinks he never does anything wrong? After another argument with my boyfriend of 4½ years, he called and asked if I was willing to change my behavior to make the relationship work. When I said of course and asked if he was willing too, he said, “No, I think I’m doing the right thing in this relationship.” How can he think he is doing nothing wrong if we have had ongoing problems for the past few years?

B.: I bite. It is the type of person who thinks the other person will change and then everything will be perfect.

Up: You two have more in common than you think.

Your “few years” translates, I guess, to three. That would mean that you have now spent more of your relationship fighting than getting along.

So I suggest another conversation. Not “What changes are you willing to make,” but instead, “I am me. You are you. Now what?” Optional changes would have happened by now, so consider what you actually have.

Do this for yourselves, for each other – and for your friends and family. I don’t know either of you and I know you both drive them crazy.

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