McMennamins Kennedy School is a very fun and unique place to eat. It's actually an old elementary school that has been turned into a restaurant and movie theater. I haven't seen movies there, but they usually show second run shows, and I think there are comfortable chairs and couches in the theater. The food is grill-style and I think there is a brew pub, but I'm not a beer drinker, so you would need to check out their web site for more info.
Have a great time in Portland!