In terms of 'Hey, let's watch some anime' it would probably be Ouran High School Host Club back in late 2008, prompted by an online friend I don't talk to anymore. Sometime in 2007/08, I watched an awful lot of Sailor Moon, though . . . I just can't remember when. So that might be my first. I didn't really start watching Pokemon until a couple of years ago tbqh.
When I was a kid, though, Zoids and Beyblade were my shows, and I loved them to bits. I didn't identify them as 'anime', though, which is why I'm not really sure whether to count them.