The Washington PostDemocracy Dies in Darkness

Carolyn Hax: Friend pressures others to fix up ‘loser’ brother on dates

(Nick Galifianakis/For The Washington Post)

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

Carolyn: 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?

— Crazed

Crazed: Wow.

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

Never mind. Rhetorical test only.

Obviously, if this man is corrupt, then you can’t play matchmaker. Done.

But disgrace, debt and depression are three D’s that leave room for recovery. Must everyone who is brought low, even by his own poor behavior, be sentenced to remain low for life? Are you really as comfortable with that as your letter suggests?

Maybe this disgraced brother hasn’t done the hard work to fill those holes he dug, or you aren’t close enough to know. Fair enough. Even if he were fully redeemed and restored to health, you’d still be under no obligation to fix him up, or anyone else, for that matter.

But you made no mention of this guy’s current state, just his past one. That alone makes a case for showing this family a little compassion, even as you say no.

You: “I’m sorry, but I won’t set up anybody I don’t know well, not even your brother.” Repeat as needed.

Her: “Why not? He’s [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 unyielding no.

Carolyn: What type of person thinks he never does anything wrong? After yet another argument with my boyfriend of 4½ years, he called and asked whether I was willing to change my behavior to make the relationship work. When I said of course and asked whether he was willing as well, he said, “No, I think I am doing right by this relationship.” How can he possibly think he does nothing wrong if we have had ongoing problems over the past few years?

— B.

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

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

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

So, I propose a different conversation. Not, “What changes are you willing to make,” but instead: “I’m me. You’re you. What next?” Elective changes would have happened by now, so evaluate 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’re both driving them nuts.