I start with the assumption that if someone wants to tell me something, she will.

Not everyday things, of course. Or basic life facts and histories. But the gray area of “possibly too personal or the black area of “highly personal.” In these areas, I shy away. If someone wants to share, I will gladly provide an ear—but I won’t inquire.

I tend to the overly emotionally sensitive, which means that I never want to make someone else uncomfortable—and I feel that asking personal or possibly personal questions could create discomfort or, at the least, awkwardness.

For example, a contact mentions doctor visits at a frequency unusual for someone just heading to annual check-ups. Or someone alludes to trouble with a family member requiring travel out of town or late nights. Or a person says something about being under a lot of stress or not sleeping well.

Of course, if close friends make similar comments, I ask for details straightaway. With friends, I don’t see any limits to inquiring about areas and issues with which I could provide an ear, shoulder, or practical assistance. The gray-area instances in question come from people with whom I have a general friendship or in-depth acquaintance or who I know through professional activities.

Yet simply because I can’t count someone in the “close friend” category doesn’t mean I don’t care about him. How can I show interest and compassion without overstepping boundaries or causing discomfort?

Remember: I tend to the socially awkward.

Some people bluntly ask questions that I would never feel it appropriate to ask—and people readily respond. I witness these exchanges with admiration and awe. That easy? Really? Should I have done that?

In fact, I’ve noticed that many people seem to expect someone to ask them about something, especially if they’ve hinted at it in conversation.

Perhaps asking would turn a light friendship into a deeper one? Perhaps the person has made the comment as a social cue for connection? (If so, it figures that I missed the hint.)

Even if the commenter didn’t mean the mention as a prompt, one could argue that no one needs to answer any question—so I may as well ask. Yet, as people don’t like declining requests, refusing to respond to a query effectively tells someone “no.” Therefore, my line of thinking has circled back to the “you might make things awkward” place.

See my conundrum?