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Yeah, sounds like he cares about you as a person. What a *********. Seriously though, I find your friend's questions to be more earnest than troubling. On one hand, The Concerned Craigslist Seller was asking weird questions about something, realistically speaking, he should no longer care about. Unless he personally crafted those tables, why does he care what happens to them next if he's been fairly compensated for them? The friend, on the other hand, most likely has a genuine interest in your wellbeing and your day to day life.
My best friend now lives in Minnesota. We both have families and jobs so we don't talk as frequently as we did in the past. If I call him out of the blue, and he says, "Hey, what's up! I was just on my way to Target". I know I'd probably respond, "Oh yeah? What's at Target?" Is this an intrusion on his life? Am I overstepping boundaries? It depends on how he responds. It's part of a conversation where we both get opportunities to drive the direction of it. I don't care what he's getting from Target, but I care that he cares about it so I'm asking. Like your friend, I'd move on if his response pushed the conversation away from that topic. I don't see anything wrong with asking friends open ended questions about their life. Maybe you guys aren't as close as friends as your "friend" thinks. If a friend asked me the questions your friend asks, I'd see it as normal. If it were just some acquaintance, I guess it could be different. I mean, you did go out of your way to say, and I'm paraphrasing, "we cool and all, but not Taco Tuesday cool."
God, I'm bored.
With my friend (who I agree is nowhere near the weirdo that this Craigslist guy appeared to be)........I was merely showing another example of having to set boundaries sometimes. After a while you can start to pinpoint patterns with people. As you alluded to, when he first would ask stuff like that, I assumed it was conversation starter / general interest type of stuff. But after a while, I got more of a "I want to see if what you were doing that day was more important than having lunch" vibe from the whole thing......particularly when he's asking about previous days in which l had said lunch wouldn't work.
Taco Tuesday sounds like a plan though. Let's do it.