Definitely not a regular. Purchased my first cigars about 2 months ago and I’ve only smoked 4-5 trying to figure out what I like. This is the list that was made for me by some folks at my local cigar shops. Any thoughts on the pairings?
View attachment 225173
Life intervened! Of the cigars that I have smoked from that list: All the Oliva's, several Montecristo's, the Ashton VSG, the Padron (they misspelled it as "Pardon" on your list), the Southern Draw, the Upmann, Camacho, My Father, Romeo y Julieta, & the Fuente Hemingway. All others, I have no experience with, but that's a great way to see the differences that the wrapper makes on a cigar, as well as looking at some of the core fillers. As for the bourbon's, I've had the Michter's, Buffalo Trace, Basil Hayden, Eagle Rare, Blanton's, Elijah Craig, Bulleit & Woodford Reserve. I'll try to comment on those, and add possible additions for you to consider.
One thing that stands out on that list is the Montecristo - I'm guessing they didn't mention anything specific, since I have yet to have a bad Montecristo. There are multiple Montecristo's, and I find them referred to most often by the band color, even though that's woefully inadequate. For that Basil Hayden, I'd recommend the Media Noche (black band) or the Platinum (silver/gray band). The Nicaraguan (also a black band, but I can't find them often enough for me to call them the black band) would be a nice 3rd choice.
I REALLY want to try the Jefferson's Ocean, so I wish I had something to tell you about that pairing, but rest assured that the Fuente Hemingway is a GREAT smoke, so if they're recommending that, it's only fueling my desire to try it. Same issue with the Booker's, and I found the My Father to be a great smoke, although hard to source around me. I got 2 from my kid when he went on vacation and went shopping for a gift for me. BOTH of those smokes will be a bit spendy, so you may want to hold off on those to see if you're a fan of pairing a smoke with your bourbon, and if you're even willing to throw that much at a single smoke from a brick & mortar (both of those ran in the $11-14 range, from what I recall). There ARE great cigars that aren't spendy enough that you feel like it's a wallet stretcher, so keep that in mind.
Both Oliva's are great picks for those bourbons, but I would advise that you make sure the Serie G is NOT the maduro version if you're going to try that with Blanton's. The maduro version has some flavors that may detract from the Blanton's, but it may actually be a good fit for the Bulleit.
For the H Upmann, I would actually recommend swapping it out for their AJ Fernandez stick with the Basil's. I dunno if I posted a pic of that one here yet, but I'll look after I post this, and if not, I'll add a pic of what it looks like. The Ashton VSG that they recommend is definitely a great smoke, but I just find them to be a bit overpriced for anything other than an infrequent treat. It's a good recommendation, but if you've only had 4-5 smokes, and you're feeling your way around, I'd hold off for just a bit. Now, if someone were to buy you one, you jump on that offer! It's a great smoke if other folks are buying! LOL I dunno on pricing for the Padron, but in my area, the same recommendation would be my advice - it's a GREAT cigar, but give it a bit for you to get your feet under you and figure out some ideas of what you're a fan of in a cigar.
I am a fan of Nub's, and thus far, those Southern Draw's I showed above. I would recommend that Rose Of Sharon with the Eagle Rare, and the Nub Dub (it's a double maduro) would be great with the Woodford's, I think.
If I missed something, or you wanted some clarification, by all means, hit me up. As with anything flavor-related, it's all relative to your personal preferences and palate. One man's caviar could be another person's S.O.S.
There's always a desire to just dip your toes in, and test the waters. In the cigar world, I would say that would be what many find in a Connecticut wrapper cigar. Those are great to start, and if you find one you like, man, that's like a diamond in the rough! Try one, and you'll see what I mean about them - smooth, almost NEVER overpowering, and they go with just about anything. That would be a great idea to try with the Eagle Rare, IMO. If you're looking for a consistent brand, Rocky Patel is an easy to find name, and there's so many to choose from, you're bound to find something you like. My personal fave from Rocky Patel is their Vintage 2003 Cameroon. The Nub Cameroon that I like is a direct result of me trying the Rocky.
The wrapper is overwhelmingly the thing that you will find a definite preference for, but try a variety, and use that as your steppingstone to see what other brands are able to do with that same wrapper. I most definitely prefer Nicaraguan smokes, but there are so many great brands out there nowadays, that "Cuban" no longer has the same cache it used to (nor should it - I've smoke some DAWGS from there, and had some Dominican smokes that are leagues better!). There's no need to spend a lot, and often, the higher price is due to something "extra" they do, like dip it in something, or put it in a metal tube, or whatever. None of these things make a mediocre smoke better, so see if they have a less expensive offering of their "bland" sticks, and see if they're a brand you're a fan of. For example, ANYBODY can make a pizza. Does someone make the generic pepperoni pizza that knocks your socks off? Those are the things you want to pay attention to. Do they make a good solid offering...and never let someone tell you that you're smoking a "kids" cigar or something that only a chick would smoke.
@WiskyDan's bubble gum cigars are hard to keep lit, but they make them for a reason - someone out there is buying them.
Last one, that Cain on the right, is another Nub. Spicy, but in a way that I really like. I would recommend that with the Bulleit or the Michters, although it's been a bit since I've had the Michter's, so that may just be one to rest on just a bit. The Perdomo 20th Anniversary would be a great pairing with the Blanton's or Eagle Rare, but first, try it all on its own without the bourbon. It really would be great with any of your bourbons 
