If the briar is wet you can tell by looking into the bowl. Wet down in the heel of the pipe (at the airway) looks... wet. A couple of smokes/day and a few days rest shouldn't be a problem for a briar - but it might be. Inspect. It's hard to get a cob wet - if they get damp or stale smelling - a day out in the sun makes things smell/smoke better.
So if your pipes are dry enough, try smoking half-filled bowls for a while to improve filling, tamping and smoking technique; try not to over compress on the fill or the tamp. Allow a draw with slight restriction but not tight-tight. And, it's easy to say but hard to do when you start out, smoke slower.
There is a balance you achieve between tobacco selection, tobacco moisture level, filling/tamping compression and speed of smoking that makes it all work out. Best way to find the balance is to practice and know perfection is just around the corner.
What are you smoking, by the way? Something from a tin, a can or a B&M glass jar? What brand9s) and where from?