With so many styles and varieties to choose from, its going to be a lot of trial and error. Generally the more age that the whiskey has on it, the more mellow it's going to be. The Scottish distillers have a saying "Time takes out the fire, but leaves in the warmth".
I think bourbons are a good place to start, because of the high vanillin compnent of the new oak barrels they use, they tend to be a little sweeter on the palate. Try cutting it with a little water (just a drop, and make sure its decent water) and avoid ice, it kills the flavor. A few people have mentioned some good ones, Woodford Reserve, I like Blantons too.
As for Scotch, if you are looking for a place to start, try Macallan 12 or 15 to start (they have a high sherry wood component to them. Also Dalwhinnie is nice with a bit of a honeyed finish. Bowmore is a good place to start for Islays, sweet and smooth with a nice touch of smokey peat to it.
You could always see if there are any tastings in the area, quite often resturants will host them, especially in Feb around Robbie Burns day.
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