It's not the complexity I'm worried about. I usually order two pints of Guinness and let barmaid wait to take the glasses away. If I drink the duration of pipe smoking, I'll be too drunk to care. I stick to Diet Pepsi.
In the summer I usually drink iced tea while I enjoy a bowl full. Cooler months, I usually don't drink anything while I smoke my pipe.
My drinking enjoyment aside from a nice Guinness at supper is usually a double of Jim Beam Honey while I sit here and read the forum
Definitely enjoy a hot, strong cup of coffee with a straight burley or straight Izmir Turkish tobacco.
If I smoke an aromatic or navy flake, nothing - Just the baccy
Bold English or Balkan maybe a dram of scotch or rye whiskey
If I’m going to have a bourbon with my pipe I keep it under 100 proof with great success. I find that a barrel proof bourbon mutes the flavor.
Barrel proof is great with a cigar though!
First pipe is always with coffe then usually just ice water. I do think beer pairs better with most tobacco than whiskey does. I do however love Balkan Sasieni with a G&T for some reason.
I can't stand dairy products with tobacco. Coffee with milk or a cup of milk chocolate. If a good black coffee, whit whisky, brandy.or a cup wine. With beer maybe only in summer, especially if it is a black, dark, or very cloudy beer...........
Coffee with my first bowl always.English breakfast tea for the rest of the day.
Cigars are a different matter straight rum with lots of ice and a nice cuban perfect.
I only drink water or wine with both pipes and cigars. Port and other sweet fortified wine are smokers favorites but I find them too sweet. Much prefer a half-dry strong new world cabernet/zinfandel or something of that sort, they pair perfectly with cigars and english blends. I don't pair beer with smoke, they always leave a dry bitter after-taste in the mouth and make the smoke bitter as well, same with coffee, which don't happen when I drink them on their own.
In the '90s, I remember cigar people talking about pairing port and whiskies with cigars. I often found these pairings didn't necessarily enhance my enjoyment on either side; the subtleties and complexities of a fine cigar and vintage port were masked or diminished.
The kinds of bourbons and whiskies I enjoy most have layers of flavour and aroma that don't seem to be enhanced by tobacco. That's not to say that I don't have a cigar or pipe with whisky, just that I'm not getting 100% of the nuance that I paid for if I pair them—if I do have them together, I'll lean towards a less refined bourbon or whisky to have with my cigar or pipe.