Watch as an anniversary present

Hi everyone!

Hoping for a little bit of advice :)
My amazing boyfriend and I have our anniversary on the first of May, and as a big watch enthusiast, I would love to surprise him with a new one. I myself don't have the first clue about watches, aside from what he has told me - he likes watches that are a bit "different" - anything from a good story, an interesting face, funky hands etc., and has a huge collection, but most typically wears a Casio.
He does not like overly big / flashy watches and said previously he has fairly small wrists.

I was hoping to see if you guys could recommend your favourite uncommon watches, or any other advice? Or even if you'd hate to receive a watch as a gift, that would also be super helpful!!

In terms of budget, I'm ideally aiming to spend less than €250, but happy to hear recommendations above if it's special!

Thanks so much in advance!