We were there for 8 nights last week and enjoyed the BFM our last evening along with a nice dinner at the Reef. That was his last show until Nov unfortunately. But he may play with Chuck at other venues so do check for that, great show!
For dining on the East and North end we loved the Rum Point restaurant, excellent lobster and pasta primavera. We took the free Red Sail cat sail there and it was an amazing evening. Unfortunately a week ago last Sunday was their last night until Oct. We were closing places down...
But the Wreck Grill at Rum Point has an excellent fried grouper BLT that is a must. Their mudslide is also the best.
The Reef Resort has a decent dinner menu along with a bar menu. The Rusty Pelican (the Reef beach bar) is a nice spot to enjoy the evening with tables in the sand.
We wanted to hit Vivines but didn't make that stop.

If you get to the West area there are a ton of excellent dining options of course. Will you be going to that area for dinner?

[edit] there should be a dj and another performer at the Reef while you are there so you will have some fun evenings.
Have a great stay on the island!