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My penpal and I have become great friends. We email about every three days, sometimes more, and in just a few months she's turned out to be one of the most positive relationships in my life. She's very polite and carefully spoken, but near as I can tell that feeling is mutual. We mostly write back and forth about about novels and poetry, with a little philosophy mixed in, and both love the 19th and early 20th centuries so we have a lot of reading in common.

The trouble that brought me here is: she's very deferential to me. There's no way to say this without sounding puffed up about myself, but she's made it clear that she thinks I'm brilliant. (She's outright said this many times. Really, I'm just observant and unusually well-read. I've tried to be honest and deter her politely, but she pushes back on that, so at this point it's become sort of woven into the mutual regard of the friendship. It's really flattering, to be honest.)

My penpal is eight years younger, and comes from a relatively impoverished working-class background where (just going from her own description) she's got almost no one else to talk about books with. College hasn't yet worked out for her, and she's a naturally reticent person. She's right there is a noticeable difference in how well each of us can read and discuss a poem or a story - she's got much less experience at it. But at her point in life, I'd had twice the opportunities and was about a third as thoughtful and a tenth as well read. She's very bright, and just as driven. I'm as impressed with her as she is with me.

I'd like to encourage her to be more forward with her own opinions. I've tried asking and complimenting but she always gently pushes it aside, and claims to be more interested in my take. Part of it is just that she has less to say, but of course that's the sort of thing that comes of time and practice. As it stands my penpal says a lot of things like: "I really liked this, but I'm not sure how to articulate it." Or: "Now that I've heard your opinion I just agree!" I often suspect her of holding back on developing her own ideas until she hears what I have to say first, and then not saying much extra.

Once again, very flattering, but it makes me worry I'm just blithely steamrolling over her own nascent approach to analyzing a text. Nothing would make me sadder than convincing her to adopt my opinions, because we're such different people and I'm convinced she'd be able to notice lots of things I don't. But I'm not quite sure what to do with that. I only know how to relate to people through ideas, and if I hold back on mine she'll ask. I'm her friend and not her teacher, so I don't want to be pushy or didactic, or come off like I'm trying to change her. (She's great as she is.) We're set to discuss some agreed upon poems soon, and I need advice first.

tl;dr So the long and short of it is, I've stumbled into an incredible penpal friendship with this extremely bright younger person. I want it to thrive, and want her to thrive, but she's very reticent about her opinions. I'd like to encourage her without being didactic or pushy. I've tried asking her and complimenting her, but she just pushes that aside. How should I approach this?

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The most effective way I've found to get an opinion out if someone who is hesitant to give it is to ask them specific questions in a narrow scope. Consider the difference between

What did you think of the book?

And

I wasn't quite sure what to think of the character Maria. Sometimes she seems like a villain, but other times I felt bad for her. What do you make of her?

The former can be overwhelming. Where do you even begin to describe an entire book? What do you focus on? What if the other person thinks your thoughts are completely silly? The latter gives something specific to focus on and also makes it clear that you consider either opinion reasonable, so sharing her thoughts should feel less daunting. Ask her a few questions like that and you should get something back.

As she becomes more comfortable, you can open the questions up by asking her thoughts about something specific but not giving her options to choose from:

I'm not sure what the poet meant by [line]. What do you think?

Again, it focuses the conversation and demonstrates you don't have any strong opinions about that part, so she should feel more comfortable giving her own perspective.

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