I have never really had a weird experience with philosophy itself, but rather with other individuals in life about it. For example; if I were to try and talk about philosophy at my school, I would be laughed at. They would completely reject me, and most likely ignore me if I were to say something as small as just saying I doubt their religion. This completely blows me off course. Why would an individual wish to be ignorant to the (possible) truth and facts? Is it because they simply cannot comprehend that their only belief could be wrong? Is it because they are just too scared of death, etc? (Do not actually answer the questions.) I have asked kids at my school if they would simply just believe in a religion if their parents taught it to them. They told me that they would believe in it if they did, and once they got to be eighteen they would still believe in it no matter how stupid it sounded. I don't know.. it's just weird.
I feel the same way, and have had the same experiences. Nobody liked that I was a philosopher, or my politics, but I ignored them and I've gotten farther than them in life. Though we are born as philosophers, people question philosophy.
Alright, as for my strangest experience in philosophy, it would have to be a scientific [or philosophical] epiphany I had one night after dreaming I was a point travelling along a parabolic arc depicting time, observing another similar arc along a different point on the z-axis. It astonished me so greatly that I jotted the image down on a notepad, believing I was on the verge of a philosophical breakthrough. I use this description vaguely because I unfortunately lost the notepad and the information I had on it. Nevertheless it amazed me, and I began having nightmares that I was trapped inside this arc-like construction similar to the earlier one, and one nightmare about some other geometric anomaly. Anyway, even if I had the notepad I doubt I could reconstruct the information in Paint or something similar.
Another odd philosophical experience was when I nearly fell into an existential crisis, but I won't explain because that may not really be too interesting.