Often when I'm making drinks for friends and I ask what they'd like me to make them, they don't have a specific answer. "What do you suggest?", or "Anything you feel like making" are common responses. While I enjoy the chance to foist a variety of both classic and contemporary recipes on willing, open-minded subjects, I hate the idea of just blindly throwing random drinks at people and hoping I come up with something they'll enjoy.
What I've taken to doing is something similar to what certain bartenders do, which is to determine what base spirits someone likes or dislikes. This usually amounts to me asking general questions like, "How do you feel about rum?", "Have you had any gin drinks you've liked?" and so on. It gives me a rough starting point, and once I've got a fix on what general categories of liquor are likely to be well-received, I can start from there and make a few other inquiries about secondary flavors (juices, syrups, liqueurs, etc.).
Obviously, the goal is to pull together a list of drinks that my guest(s) will likely find appealing. However, once I have an idea of their tastes, I also sometimes use the opportunity to re-introduce an ingredient that they don't care for...and attempt to redeem it for them with creative mixing. And there is probably no other ingredient that I take this approach with more so than whiskey.
It's been my experience that of all the base spirits, whiskey is invariably the hardest to get people to embrace (Gin and Tequila are contenders, but I can still find people more willing to take the leap with those). The reasons are legion... Past overindulgence, unawareness of quality product, aversion to strong flavor, and so on. Whiskey also suffers from a fearsome reputation as rough-edged firewater able to be enjoyed only by those with iron stomachs and epic tolerance.
I've found that the best approach to dispel these impediments to whiskey appreciation is to go gently. If someone is iffy about whiskey, plunking down a Bourbon & soda or a scotch on the rocks won't likely get you very far- it's the cocktail equivalent of throwing a nonswimmer into the deep end of the pool.
What I like to do is start with something like Irish whiskey, which as a category I find to be a bit softer, mellower, and more accessible than other whiskies. As much as I love Bourbon, rye, and scotch , they can be a bit ambitious for a newcomer. Canadian whiskey can be a good option as well, but can vary in flavor and quality, so I recommend trying a few until you find one that isn't too intimidating.
At that point, it really becomes matter of experimentation. Though not as plentiful as Bourbon and rye-based cocktails, there are many drinks containing Irish whiskey, and any decent bar guide or online drink recipe resource should yield several good options. Sample as many as you reasonably can and note how strongly the whiskey character evidences itself... and make notes for future reference.
Or you could do what I often do: create an original drink! Aside from being tremendous fun, it allows you to finely tailor the flavors & proportions to suit the taste of whoever you're serving. Whiskey pairs well with such flavors as vanilla, cherry, apple and various herbal liqueurs just to name a few. Cream liqueurs also work very well with most whiskeys, and they lend a sweetness that rounds the corners off the brown stuff. Tinker with abandon and enjoy the process!.
That's how I arrived at the following recipe, and I've had success serving it to the whiskey-averse...
~ A Dr. Bamboo original creation