This is a hard one for some people. The thick,smoky flavor seems to turn off a lot of people. I remember getting a glass of something that tasted like it would be much better as a dipping sauce for chicken and steak than something to be taken directly.
But it turns out that there are multiple types of Scotches out there, and they are from various parts of Scotland. So yes, there's the smoky barbecue ones, but there are also the lighter floral ones. I haven't researched Scotch well enough to tell you which regions have which flavor characteristics, but I can tell you that Glenfiddich 12 is a great start. It's not overly smoky and can be sipped neat or on the rocks.
The longer it's been aged, the mellower the flavor. There's a certain harshness to Scotch, I find, so this mellowing is desirable to me. I try to aim for 12 years, unless I'm feeling spendy. I've purchased a 21 year old bottle, but didn't enjoy it proportionally more. It was around $110, but I would have been better served by three $30-40 bottles.
Sometimes you'll find that it says it's been matured on sherry or port (or others). This indicates that after it sat in the barrel for X years, it was placed in a second barrel that was used to age that named alcohol. It will then finish in the second barrel for a few months before bottling. I've only had sherry finished once, but it didn't make a good impression on me. I've had friends drink the same bottle with me, and they liked it. Port and sauterne are good though. I've also had some good luck with rum barrels.
There's single malt, blends, etc. Single malt costs more, and it's good. Blends can be nice, but not necessarily. They tend to be cheaper though, so maybe you could start with a blended 12 year old Scotch to see if that appeals. Save some money that way.
That's another thing. Scotch is pricey. A quality vodka goes for about $30 a bottle. A fine bottle of Scotch goes for that price. I've routinely spent $45~50 for a good 12 year. I think it's worth the money, but you may not.
Story time children (but hopefully no actual children are reading this).
My friend Nate loves smoky Scotches. The smokier, the better. Me, not so much. But he did recommend smoking a nice cigar with them. The idea is that the smoke of the cigar will overpower the smokiness of the Scotch, like eating candy and then drinking soda. But instead of getting a mouthful of crap-tasting swill, the other flavors are brought to the forefront. Scotches are rarely a one-trick pony.
We did a cigar, Scotch and Archer night at my place (wait, I had something for this). I should have taken a picture of the table that night. I think we had 10 bottles. We started lightest to heaviest. When it came time to hit the super smokies, we did a taste pre-cigar. It was overwhelming. We went to the patio to smoke, bringing our glasses, and the bottles because why not.
Outside, we lit the cigars and just enjoyed their aroma for a while. Finally, I grabbed my glass and took another sip. Wow, what a difference. I tasted orange and spice, and some other stuff, I'm sure. You're probably thinking it was just due to the Scotch breathing. I wondered that myself. I poured a fresh finger and gave it a sip. It wasn't quite as good as the glass that I just finished, but I definitely could taste the flavors under the smoke.
A few more glasses were had. Stories told; jokes swapped; cigars finally stubbed out.
We resumed inside, re-visiting several bottles and finishing off the marathon. Soon the sun came out. We had been up all night drinking Scotch and smoking cigars. Hardly a bad way to spend 8 hours. I fished out two cigarettes and we called it a morning. He said he was OK to drive, and he seemed like he was.
I got a text saying he was home. I went to bed. I knew I'd have to clean up later. Much later.