I was talking to this girl on the phone, and our conversation shifted to past experiences. She asked me if I had any stalkers in the past, and I said yes, the at one point, she joked that if her cat could talk, she’d be in trouble. I laughed, and she told me a story about male strippers, which I listened to without any judgment and even encouraged.

Later in the conversation, she mentioned the cat thing again, so I asked her, “What’s a story your cat would share that would get you in trouble?” She seemed surprised, got a bit awkward, and just said, “I don’t know.” I didn’t press and moved on to other topics.

Here’s the thing, I genuinely don’t judge and actually try to make it comfortable for women to share things openly; part of it because I myself have my own experiences. But it made me wonder: Why would she be surprised or awkward when I followed up on something she brought up herself? Do you think the way I asked made it feel more intense than it should have been? How do you usually navigate topics like this without making things weird?