Flip that sucker over and look at the bottom. The bottom of the pineapple should be a bit softer than the rest, and it should smell the sweetest. If the bottom is moldy, wet, or looks like it’s been in a bar fight, run away.
A great pineapple’s bottom is like the perfect handshake—firm but friendly. A bad one is like a sweaty, clingy grip that won’t let go. You deserve better than that.
Pineapple Ripeness Chart: How to Pick a Sweet & Juicy Pineapple
And while you’re down there, check the little “eyes” on the skin. They should be plump and well-defined, not shriveled or sunken. Shriveled eyes are a sign of an old, tired pineapple that has seen better days in a fruit basket.