Well you've got a couple legitimate recommendations here... Fat Tire and Blue Moon though? I mean, they aren't bad, and it's certainly better than anything he's ever had... but nothing special. Before trying an IPA, I'd recommend trying several different pale ales to warm you up. Once you find a good pale ale, you can step up to the IPA and find something you like there.
Youngs Double Chocolate Stout is certainly delicious, and goes GREAT with a steak, as do most other stouts. Also goes great with a cigar //content.invisioncic.com/y282845/emoticons/wink.gif.608e3ea05f1a9f98611af0861652f8fb.gif
What you will find with a better beer, is that they generally have a higher alcohol content, so you don't need to pound a 12-pack to get a buzz. And you won't be chugging them like crazy. But a 6-pack of a good beer can get me through most the night.