It sounds like an advice columnist’s philosophy review: “Who’s worse: the loser, the myopic control freak sister who defends him, or the person who befriends the myopic control freak sister , but who obviously doesn’t like it?”
No matter. Rhetorical test only.
Obviously, if this man is corrupt, then you can’t play matchmaker. Do.
But disgrace, debt and depression are three Ds that give way to healing. Should anyone who is humbled, even by his bad conduct, be condemned to remain humbled for life? Are you really as comfortable with this as your letter suggests?
Maybe that disgraced brother didn’t do the hard work to fill the holes he dug, or you’re not close enough to know. Fair enough. Even if it were fully redeemed and restored, you still wouldn’t be obligated to fix it, or anyone else, for that matter.
But you made no mention of this guy’s current state, just his past. That alone justifies showing a little compassion to this family, even if you say no.
You: “I’m sorry, but I’m not going to frame anyone I don’t know well, not even your brother.” Repeat as needed.
She: “Why not? It 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 unyielding no.
Carolina: What type of person thinks he never does anything wrong? After yet another argument with my boyfriend of 4 and a half years, he called me and asked if I was ready to change my behavior to make the relationship work. When I said of course and asked if he also agreed, he replied, “No, I think I’m doing well with this relationship.” How can he think he’s doing anything wrong if we’ve had persistent problems over the past few years?
B.: I will bite. He’s the kind of person who thinks the other will change and everything will be perfect.
Upside down: You have more in common than you think.
Your “few years” translates, I guess, to three. This would mean that you have now spent more of your relationship fighting than getting along.
So, I propose a different conversation. Not “What changes are you ready to make”, but rather: “I am me. You are you. And then ? Elective changes would have already taken place, so assess what you actually have.
Do it for yourself, for each other – and for your friends and family. I don’t know either of you, and I know you’re both driving them crazy.