Carolyn Hax: Should a sister speak now or hold her peace?

My brother is evidently okay with this. He adores her and has self-esteem issues dating back to childhood.

If he’s happy, do I just need to be happy for him? As someone who thinks he deserves someone who really loves him and thinks marrying him is a great end unto itself, do I owe it to him to suggest that he reconsider? Or do I just keep my mouth shut and prepare to spend the rest of our lives (or the length of their marriage) faking happiness for them?

— Settling?

Settling?: I can see why you don’t feel like celebrating, but . . . at least she was honest?

As I’ve said repeatedly, I think we get one shot at questioning the choices of people close to us. This represents the overlap of two often-contradictory truths: The first is that the people who love us most are sometimes able to see things about our lives that we can’t, and if we trust them to have our well-being in mind, then we can trust them to wake us up when we need it. The second is that no one else can know what we really think and feel — or how things will turn out — and so the most loving gesture is often to zip it and trust our judgment.

So: If you really really think an alarm needs sounding, then have one conversation before you scoot back to the sidelines where you belong, cheering on loved ones regardless.

I’m not sure anyone needs to ring a bell Annie has already rung herself. Your brother knows what he’s getting into as well as you do. But if you still think it’s important to say something: “I know you’re nuts about Annie, and I think she’s great, too. I just want to say this once, and I’ll shut up ever after: I think you deserve someone who loves you as passionately as you love her and thinks marrying you is a great end unto itself.

“Okay, I’m in the shutting-up phase now, wishing you nothing but happiness.”

This assumes, by the way, that your brother has talked to you about all of this, about Annie’s plan to marry now and fall in love later. You do seem to have a lot of detail. If you’re working off impressions, rumors and third-hand material, however, then that’s another good reason to hold your peace and trust him to figure it out.