Getting into Scotch can be like getting into wine or cigars for the first time. So many different ones and you can really like one while really disliking another.
Some quick pointers.
Islay Scotch is very peaty. Some, like Laphroaig can literally take like a dirty ashtray. Some people actually enjoy Islay Scotches. I'm not one of them.
The suggestion for Highland Park 12 year old is a good one. Easily a really nice starter Scotch to get into before you try anything a little wilder. I always have a bottle of Highland 12 on standby.
This next tip might be met with a little scorn from some as lots of people are very particular about how to drink it. Some purists will say that "neat" is the only way. I completely disagree with those people.
All Scotches benefit from just a slight addition of either simple water or, as I prefer, a single ice cube. This is even more true of cask strength Scotch which has much higher alcohol %. The water (just a teaspoon if that) or ice cube, as it melts both serves to open up the whiskey and it even takes a very slight edge off the "heat".
For a great example of the transformation that a Scotch can go through, take a Scotch like the Glenlivet "Nadurra" 16 yr cask strength (57.7% abv) and drink it neat. Then take the time to let an ice cube melt in it and try it again.
Scotch is great and a great friend of cigars. Enjoy! :ccool: