Poole's Diner has never let my wife or me down. Most of the menu is constantly changing, so I cannot suggest any particular entree, but I have NEVER been disappointed. Some meals have been better than others, and I had a sample of my friend's royale (one of their staples) that I found a bit salty, but I have had the best scallops I have ever had here and some fantastic steak tartare and very good everything else. The desserts are ALWAYS worth it along with an after-dinner coffee. I typically get the chicken liver pate for an appetizer (don't be afraid to ask for some more crostinis). Service is always knowledgeable and friendly and reasonably fast. The hostess sometimes recognizes me and there's this fellow--I don't know if he's the manager or what--he's always very friendly and makes me feel like an old friend when he asks how I am in passing.
Some notes: My wife is a vegetarian. There's not necessarily a whole lot of protein on the menu for her, but she is extremely satisfied getting sides and apps and getting her protein from cheeses. She drools over their brussel sprouts and beets.
Cons: Long wait times. They don't take reservations except for Valentine's Day and New Years. If you show up around 7:00 on a Friday or Saturday with a party of 2, expect to wait at least 40 minutes usually, unless there's an opening at the counter. With a party of 4, potentially 60-80. And larger than that, make sure you're in good company because it could be near 2 hours sometimes. But you can purchase beverages to pass the time and stand just outside the door to drink them if it's a nice evening. It can get a little loud indoors sometimes.
Beer menu is limited. They only keep two beers on tap and the rest are somewhat expensive bottles. So I typically resort to wine/cocktails which are all quite delicious and they definitely don't skimp on the liquor.
My wife and I go probably once a month. With at least 2 drinks each, an appetizer, two entrees, 1 or 2 desserts, and a coffee, we typically spend about $100 a visit.