Uh...no, I've never brought a flashlight somewhere and felt silly for having it. Then again, I carried a Victorinox MiniChamp with me in high school -- I even loaned it to a teacher a couple of times. Would've been an automatic 2-year suspension if I'd been caught. Talk about feeling silly, I'd have felt damn silly if that had happened. Fortunately I had the good sense to not misuse it, and nothing bad ever happened. Funny how that works.
Unfortunately the Anglosphere is moving steadily in the direction of adopting the attitude that only experts and professionals have any business being equipped to handle unusual circumstances. Somehow that even extends to tools that have no feasible use as offensive weapons, such as flashlights. Most English-speaking countries are "ahead" of the USA in that regard. There are stories on here of Australian cops hassling people for having flashlights brighter than the ones the cops had. Ticks me off to no end.
I've definitely gotten a few odd looks for having a flashlight at work, and a few odd comments as well. I return the odd looks, and the odd comments I respond to with a reminder of the most recent power outage and how I was the only person on my floor of the building with a flashlight. I don't need a specific reason to carry a knife, or a multi-tool, or a flashlight, any more than I need a specific reason to carry a pen, and I refuse to entertain any suggestion that I should need such a reason. Being accosted for carrying a pen that could be used to stab someone when I don't have a specific need to write something on a given day might sound like an absurd scenario, but as long as people willingly back down whenever questioned about their personal effects, someday it won't be absurd at all. After all, couldn't you just send a text message? It's safer than using a sharp pointy pen.