I can see it. Especially if he does have some romantic interest in her. There’s the worry if the subtext is that the reason I’m sending this whole article to you is about #9.
Just not enough upside for the potential downside.
Nobody said anything about a romantic interest. Most people’s relationship with people of the opposite gender are not romantic at all. Why would this be relevant to bring up?
It's relevant to bring up because he said it would make him feel awkward to send it. You'd be right if he didn't think it would be awkward to send and he had no romantic interest, even less awkward if he knew she had no romantic interest. But at this point the only thing we know is that he did feel awkward about sending it. Hence the relevance.
i see the relevance, but i don't see the problem, especially if he himself isn't in academia. he could convincingly argue that he isn't part of that mess and especially won't benefit from it.
Just not enough upside for the potential downside.