Tell Me About It: Unsolicited advice to a beloved sister?

Adapted from a recent online discussion.

Question: I usually hold my tongue when it comes to dishing out unsolicited advice, but I'm curious whether that policy holds with someone I love.

My sister is a wonderful in many ways, but has trouble dating men for longer than a few weeks. I have a few theories: She thinks she comes off as loose and carefree, when actually she exudes how high-strung and sensitive she really is; and her default conversational topic is complaining about other people.

Would a caring sister say, "I know you haven't asked my opinion, but maybe if you tried to find other topics" or "If you let the little things the guy said or did wrong go, you'd find more of what you're looking for"? Or do I just say nothing, remain supportive, and offer my opinion if she does ask?

Answer: The hold-your-tongue policy holds double for people you love, since they're presumably the ones you'll most regret alienating.

I'm also not sure what you'd accomplish with your theories except to put your sister on the defensive. Silence isn't the only alternative, but what you propose is close to suggesting she change her temperament and personality, when what you want is to actually help her, i.e., minimize pain and maximize pragmatism.

One way to avoid the unsolicited trap and remain realistic is to wait till she complains, then ask her what she thinks went wrong. Ask what she plans to do, how she thinks her actions will be received, etc.

Maybe her lens is too warped for this to yield good suggestions, but, if nothing else, that would tell you her lens is also too warped for your theories to have your intended effect.

Ideally, some prompts will get her thinking, plus the ideas will be hers, so automatically less painful. Best of all, you can wade in gently with questions, and back away if it doesn't work. With blurting out an opinion, there's no taking it back.

Last thing. While it can be useful to hear about aspects of ourselves that we can stand to improve, I think it's even more useful (and far better for one's confidence) to hear about the good stuff we'd do well to focus on and highlight around others. Right now, it sounds as if you can't see why a guy would want to date your sister, when it might help her most if you could help her see, and cultivate, why one would.

Comment: My sister always gives me some. Infuriating. Many years ago, before marriage, kids, etc., she said to me: I think you should date more. My answer was: Oh, yes, I do too.

And she was speechless. (If you knew her, you'd know how impossible that is.)

She thought I would argue with her, when by then I was so tired of that. Yes, she thinks we are oh-so-close. You probably think you and your sister are - when, with questions like that, you probably are not. Just some unsolicited advice.

Answer: Yep, that's the alienation I'm talking about. And if I'm ever in a slapfight, you're on my team.

Chat with Carolyn Hax online at noon Fridays at www.washingtonpost.com.