It's just a hunch, and I can't prove it beyond anything anecdotal, but I'll say it here for the record: I think a lot of the initial aversion people have to whiskey in general comes from starting out with bourbon.
This holds especially true in America. Here, bourbon is a cultural signifier. It's the drink of cowboys and other men who do rough, honest work and aren't afraid to get their hands dirty. It's a product steeped in history and unique to this nation. Meanwhile, scotch seems to be the drink of those who are both stuffy and moneyed, and clear spirits seem to have an aura of femininity, or they just seem European. Men who aren't yet drinkers imagine themselves with a good pour of bourbon and like what they see.
In an American bar, you also cannot throw a cat without hitting a bottle of bourbon. For my twenty-first birthday, I remember I ordered a Jack and Coke in a Vegas steakhouse. In that moment, it seemed like the perfect combination of an inviting, American drink that a young man would order. As is often the case, what works out in theory doesn't often hold true in practice. By this I mean my dad had to finish the drink for me.
Where liquor is concerned, bourbon has almost a "Christmas Story" kind of thing going on with it. By this, I'm referring to the scene when Ralphy is sitting on Santa's lap, stunned by the surreality of the experience, and temporarily forgets what he wants for Christmas. "With unconscious will," Ralphy narrates, "my voice squeaked out football." It just seems like what we're supposed to be having.
But the reality is that your average-grade bourbon is going to be way more rough and tumble than a quality scotch. The corn, which will at least make up 51% of the distillate—although for most bourbons, it's usually somewhere around 70~80%— imparts a distinctive kind of funk to the spirit. Additionally, since bourbon needs to be aged in new oak barrels, you're getting a lot of wood influence, which to the uninitiated can be tannic and bitter. Lastly, most bourbons are high proof as a sign of quality, so if you start off asking for "the good stuff," you're likely to be poured a slug of something in the 50% ABV range, which will be bracing to a newcomer, to say the least. And, of course, they'll drink it neat their first time out, because again it seems like that's what they're supposed to be doing.
Okay, so what should we do?
If you're interested in cultivating (or helping another cultivate) a taste for whisky, I'd look for a quality Irish whiskey, a non-peated Scotch, or something Japanese in nature. Respectively, Jameson Black Barrel, Monkey Shoulder, and Akashi White Oak are three great choices in the $30 range, but as you might guess with this site, that list is by no means exclusive.
When it comes to how to actually drink, ice is a good friend to the novice whisky drinker. Contrary to what's de rigeur these days, I'd actually recommend crushed or pebbled ice to dilute the drink faster rather than throwing in one big-ass ice cube the size of the hope diamond. And, most people think you're supposed to gulp the shot down like a cowboy. Even newcomers will find that whisky is a lot less bracing sipped a little at a time, and held in the mouth for several moments before swallowing.
Yes, but like you said, I want to drink Bourbon and I don't know why exactly!
Sure! Because what's more American than that? Had I been able to reach back through the void of time and hand my 21-year-old self a sweaty rocks glass of bourbon, I'd probably go with Evan Williams Black Label, Maker's Mark, or Old Grand Dad Bonded splashed with enough water to get it down into the 35% ABV range. For me, all of these hit that sweet spot of what a good, timeless bourbon should be like without being too much of any one particular thing. However, I always have your back and you can clicken unto thineself thusly to see what else I love in the category.
And hey, trust me: I know culture and tradition is hard to shake. There's a saying I like: "The fish are unaware of the water." None of us starting out really know why bourbon is the de-facto man liquor here in the US, but it is, and most of us spend several years pretending we like it when in fact we barely tolerate it. If that doesn't sound like you, I'll piss off, but I wonder how many other whisky drinkers we'd have if everyone and everyone didn't gravitate toward bourbon like moths to a bare light bulb.