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My vote has to go to Phanpy because it always reminds me of an old iconic clip from a YouTube video I watched years ago, and a few friends I've gained and lost over the years bonding over that.
But Teddiursa is wonderful and I have to shout out its early appearance in XD Gale of Darkness which helped me appreciate it a lot more.
they're both cute! though yeah, I have hardly used them either. I think my only time using Ursaring was recently in a challenge run here, though it didn't start out as the cute teddy since I caught it evolved lol. Phanpy was my favorite when it came to the anime though.. Ash's was cute :3c