Oy...Anna's is a 5 dollar burrito joint....not Mexican food.
Zear back to Waltham - check out Biagio's. Pretty good restaurant - family owned and well established. The Skellig is a good little Irish Pub and they have some decent live music. Across the street from the Skellig is a place called Magarita's if you are looking for 21 year old drunk sluts - great place for that and drinking Magarita's. Don't eat the food there as it sucks. On the other side of the Skellig is a little hole in the wall called Sadie's. It's a dirty little bar but they have some pretty decent bar food (wings, skins, and tips come to mind). If shooting stick is your thing you can check out the Wave, that is closer to Belmont and a little more of a drive. It's in this big complex. They have a couple dozen metered pool tables, darts, ping pong, big ass bar - etc.
If you hit 95 and go north to Burlington (Exit 32) you'll have a lot of restaurants and shopping if that's your thing. There are also movie theatres everywhere including an IMAX north on 95 about 20-25 minutes in Reading.
If you want to hit up some place nicer for dinner I can throw out a few suggestions for that too - or if you have something in particular you want...shout out.