8. Dating Vicki Vale
...was maybe not the smartest move Bruce could've made. Bruce Wayne's romantic relationships have never been terribly mature -- this is a guy who can barely connect with the web of associates who form his "family", much less with a mature, responsible woman -- and most of his romances with "normal women" (Silver St. Cloud, Linda Paige, Julie Madison) end bittersweetly at best and tragically at worst. But at least none of those women were actively trying to figure out what Bruce Wayne does with his nights. At least when Superman was romancing the reporter trying to suss out his secret identity, they were already working together (and she was apparently blind enough to not be able to see past his glasses); Bruce Wayne purposefully seeks out the reporter who would give her left arm to be able to splash Batman's secret identity all over the front page of the Gotham Gazette, and then ends up
shocked (in Gerry Conway and Gene Colan's quite underrated Detective Comics run) when she tries to do just that. Special idiocy props to Bruce for not making this mistake once, but twice, the second time with reporter Vesper Fairchild, who was
also researching Batman's secret identity. Vicki got off lucky, though;
Vesper ended up getting killed because of her relationship with Wayne.