Carolyn Hax: Kindly airing differences can help cement friendship

Hey Carolyn: I’m a nose-to-the-grindstone type with a steady job, on track with savings for a comfortable retirement. I have a very dear and close friend who’s kind of the opposite – flits from job to job and career to career, lives hand-to-mouth, and is barely making it. She dreams of striking it rich someday with a brilliant entrepreneurial coup.

When she comes to me with Yet Another Brilliant Idea, what is the role of a friend? Encourage her to chase yet another unicorn, or try to bring her back to (my conception of?) reality? I’ve tried both ways, and neither feels right. – Odd Couple

Have you ever asked her?

I can think of 40 ways to broach this topic, about 39.5 of them some mix of awkward and patronizing. However, if your motive is genuinely to be the best friend to her that you can be, then trust your tone and your fondness for her to carry you through.

Maybe: “I never know how to respond to your ideas when you present them to me. We have such different styles – I plod, you leap. Right? So I always see your ideas from the perspective of a plodder, and think, ‘No way!’

“But, obviously, you’re not me, so I’m left groping for something to say. Do you want me to share my perspective? Or would you rather I just nod and listen?”

Now, it’s possible she’ll welcome your grounding influence in theory only to resent it when the practice of it hits. At that point you can add 2 + 2 and go back to nodding along. Think warmth, not perfection.

However, having talked about it before will give you the language to address it again, if you think that would help keep you close: “I know you said you wanted my killjoy perspective, but I get the sense it’s not as welcome as we had planned. What do you think?” Your differences push you apart, yes, but openness about them gives you ways to be in that together.