Sherry. I like Great Western dry sherry, not very sweet, a lovely warm nutty taste. They say all alcohol has the same effect, but wine gives me a headache, hard liquor makes me ill, beer revs me up. But sherry, like putting on warm fuzzy slippers.
Someone not particularly used to the taste of even fine liquors is probably going to find whiskeys and bourbons a little… harsh. Liqueurs are probably a better choice.
But try a decent cognac in a bar or restaurant setting to see if it suits, first. If it’s too strong or “medicinal,” amaretto/Tia Maria/Kahlua/Chambord or another liqueur with a stronger flavor-flavor over alcohol might be a good choice for the next step. Then cognac. Once you’re accustomed to that, try a few varieties and eventually try a good bourbon.
I don’t care for liqueurs myself - my rule has pretty much always been “if you can’t drink it straight, don’t drink it.” So getting away from blender drinks that are mostly fruit juice could be seen as saving a soul, here.
Sambuca, with three coffee beans (health, happiness and prosperity) and set alight is a nice sipping drink. I’m not saying this is the perfect drink for you, just that the options are very wide. Another nice sipping drink which isn’t drunk widely is Chartreuse - yellow or green - flavored with over 100 herbs, spices and flowers. It was initially produced in Voiron, France from a mixture prepared by Carthusian monks, the recipe was given to the monastery in 1605, although the first batch did not come out until 1737. That recipe has long been shrouded in mystery and, to this day, one of the monks who was asked what goes into that base elixir said “hamburger and goat cheese.” In other words: we’re not telling.
I’m not normally fond of sweet alcoholic beverages, but I do have a taste for Drambuie. It can take little getting used to, but I prefer it over coffee, mint, and other flavors.
Even as smooth and warm as a good bourbon is to an accustomed drinker, I think most fruity-drink drinkers will find it a tad “medicinal.” But it’s worth a try, especially something a little better than the JD tier of brown.
Just make sure SOMEONE drinks it and appreciates it.