Just turned 21 and my father is the only whiskey enthusiast I know personally. But he's into some really expensive and "acquired" tasting bourbons. From my limited googling, Jameson is the way to go? I only really have had Evan Williams from my college days
I would personally recommend Rebel 80 proof as a good starter bourbon. Sweet, soft, nice caramel flavor, and very cheap. I recently had my brother – who has never tried any whiskey neat before – give it a try and he actually said it was "nice" and it didn't burn at all. A couple others to try are Old Forester 86 proof or Benchmark Top Floor. All very affordable easy sippers that also have higher proof versions when you're ready to step up a bit.