If you think Montclair seems to have a bunch of stuff to do (check out the billiards and other theater entry), you're right. Montclair is a fun town to hang out in if you've got nothing to do at night; of course one street can't compare with all New York City has to offer, but Bloomfield Avenue in Montclair does have some great restaurants, a fun cafe, movies, theater, and other things. 12 Miles West is a small theater adjacent to the Clairidge Cinemas. I've only seen one show there (it was an improv show), but the theater is an intimate place, and it seems like a good spot for a date, coupled with one of the restaurants somewhere else on the street.