Smoking Cigars
A few quick tips on getting started coupled with some self-reflection on allowing yourself to enjoy things.
I started writing this newsletter from a cruise ship. After spending a week on a boat in the Caribbean with my family, I took an hour on the last day to duck out and have a cigar alone. For those who are curious, it’s a Por Larrañaga Petit Corona; I bought a box in 2020 right before Cuban cigar prices went through the roof and this is the last one. It’s aged really nicely and I am pretty sad that I don’t have any more, especially since they’re now going for 3-4x the price I paid.
I’m guessing that most of my readers don’t smoke cigars, nor have much of an interest in them. And I am also very much aware that cigar smoking, to a lot of people I know at least, can come off as kinda swagless. Flip through any Cigar Aficionado for all the evidence you need; it’s an unnecessarily testosterone-loaded industry that makes me feel a bit out of place. There’s even an organization called CRA that exists to fight for an American’s rights to smoke cigars in the face of the “anti-tobacco movement” whose language and branding feels very right wing persecution complex-coded. I only know about it because they were doing a fundraiser where you’d get a sampler package of cigars in exchange for a donation to the org (and yes, I bought it because it was too cheap to pass up).
Cigar lounges are central to the whole aesthetic, even down to the vibes. On more than one occasion I’ve personally heard some guy roll in crowing the tired trope of “what’s up guys, my wife was nagging me and I had to get out of the house.” I’ve also often wondered why every space looks the same. There’s nothing inherently wrong with leatherbound chesterfields and rich mahogany cabinets but the lack of creativity gets pretty old.
I have two responses to this. Firstly, let me venture this counterpoint: most things in life can be corny. Knowing this, I think a key component of allowing yourself to enjoy something is to not be wholly guided by the way others partake of it; you need to have the backbone to indulge your way. This comes into play with regard to fashion all the time - for instance, have you ever soured on a particular garment because you saw someone wearing it poorly? Why not just have confidence in the fact that you’ll style it differently through your own lens? And secondly, I think there are a few of you out there who are at least mildly curious about cigars. The idea of writing about this topic actually came to me a few years back; when occasionally posting IG stories while smoking, I started to get DMs asking about what cigars to try and how to get started. I did my best to answer those questions but sharing those tips here seems like a much easier and thorough way to do it.
I’ve been smoking for maybe 18 years now and was introduced to this hobby through friends. One in particular - Wilson - would come visit me at Self Edge NY during its early days and bring new cigars for me to try. We would drink coffee and smoke on the bench outside when the shop was slow, which really allowed me to expand my palate and discover what I liked and what I didn’t. Those were really special times and I cherish them deeply, especially since Wilson passed away a few years ago. My ongoing love for cigars is a gift that he left me.
I have another memory that stands out for me. Kiya, Demitra and Johan were visiting NYC in the fall of 2013 and we took an afternoon to hang out in Red Hook. We ate lunch, perused shops, and explored the neighborhood; at one point we stumbled across a cigar shop in a beautiful brick storefront.
The gentleman working the shop was named Yakub and he told us that it was a Nat Sherman pop up situated inside the Widow Jane distillery. As a big Nat Sherman fan, I was surprised to find a shop like this on such a sleepy block in a quiet but very cool neighborhood. We spent hours there, ordering drinks from Widow Jane’s cocktail bar around the corner, smoking cigars, and chatting with Yakub as the sun went down. It’s a moment I think back on fondly.
To summarize the reasons why I enjoy smoking, cigars afford me the opportunity to slow down for an hour and get off a computer or a phone (*sometimes* - a cigar and a doom scroll can be a pretty great combo). I’m able to take time to rest, think and reset. Smoking has also expanded my palate and has taught me to search for notes and profiles that are helpful to understanding what I also like in coffees, wines, and food. And lastly, it provides an excuse to get together with a friend and catch up.
A few caveats before I get into some beginners tips. While I have been smoking for many years, I’m no expert. I don’t smoke nearly often enough to have a wide breadth of experience, and my palate is not so refined to be able to differentiate between all the minute details of every cigar I do smoke. I know what I like and what I don’t like, and that is probably the simplest but most important suggestion I can offer. You have to trust your taste. More on that below.
📝 Some Tips to Get Started
1. Ask a Friend
A benefit of indulging in a new vice is the shared experience. If you have friends who smoke, just ask to join them sometime. Beyond the obvious social benefits, they will be able to suggest a good cigar to begin with and even walk you through how to smoke it. If you don’t know anyone who smokes, then the rest of this information is for you.
2. Toss Old Cigars
If someone gifted you a cigar and it has not been properly stored (if you’re not even sure what that means then the answer is a hard no) then you should not smoke it. Cigars are not like cigarettes where they are shelf stable; the tobacco leaves are of a much higher quality and need to have been stored with proper humidity to be enjoyable. A dry cigar can taste acrid or bitter and will burn unevenly. One quick way to tell if your cigar has dried out beyond use is to give it a gentle squeeze - if you hear the leaves crackling or even worse, the wrapper itself splits, you gotta toss it. It’s time to start over and get something new.
3. Visit a Shop
I spent some time above clowning on cigar shops but they still play a very important role in honing your taste in the same way that a good wine shop would. Don’t go to a bodega that has a poorly maintained humidor full of skunky smokes, go instead to an actual cigar shop or lounge and tell the staff “I’m new to this and I’m not sure where to begin.” And on your second visit, tell them what you had your last time and what you liked and didn’t like about it. They’ll guide you towards what to try next.
The shop will also teach you the basics of how to prep the cigar to smoke. First you’ll have to cut it, either with a cutter or a punch. People have different preferences on how much smoke they want to draw out of the cigar and how much they want to taste, which is what accounts for different cutting methods. Pick one and stick with it for a bit and then start to experiment. Then you’ll need to light it, preferably with a butane lighter or a wood match so as to not pollute the taste of the cigar (full disclosure: I’ve used a Bic in a pinch and did not notice any difference).
One last thing that I would suggest when getting started is to opt for a smaller cigar size. I personally always stay in the range of Corona and smaller; my sweet spot is a cigar that takes me an hour or less to finish. If the shop staff tries to push a “gorilla dick” on you (as James Harris likes to call them) just politely decline and ask for a Petit Corona or a Robusto instead. You’d rather finish the cigar and look forward to the next one than spend more on a massive cigar and have to toss it (or worse yet, finish it and feel gross).
4. Smoking the Cigar
My apologies if this seems super basic, but you’re not meant to inhale cigar smoke. It’s true that some people do but that’s just psycho behavior. Cigar smoke is way more intense than cigarettes and the point is to taste through your mouth and nose, not by drawing it into your lungs. Don’t puff on it repeatedly; instead take a long, continuous draw every 1-2 minutes and let the smoke linger in your mouth for a few seconds before letting it out slowly. Another thing to keep in mind is that it’s ok to let the ash build up on your cigar vs constantly ashing out on a cigarette. A stack of ash at the end of the cigar is desirable because it cools the air coming into the cigar, allowing it to burn cooler. Eventually it’ll get to an untenable length and you should just ash out.
Pacing is very important; if you draw too often, you’ll feel sick from tobacco poisoning and the cigar will burn too hot. Wait too long in between draws and the cigar will go out and you’ll need to relight it (this happens to everyone; just tap the ash off and relight it). It takes time to develop a good rhythm for smoking - one thing I employ to keep a cigar lit even if I don’t feel like drawing in the moment is to just blow smoke out through the cigar. This keeps it burning without having to continuously draw.
5. It’s OK to Stop
This piece of advice was given to me by a friend and it was so helpful and freeing. When I first started smoking and was given a cigar by someone else, I felt the obligation to finish it or else I would be wasting it. He quickly corrected me and said that if we are not enjoying something (anything, really) that it’s ok to just stop. If you’re drinking a cocktail and it tastes awful, you’re under no obligation to finish it. Same goes here. The cigar can also be enjoyable early on and after half an hour, you’re no longer into it anymore. It’s ok to put it out and toss it. Even a cigar that you don’t like will give you information to further hone in on what you might want to try in the future.
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Hopefully that’s enough to demystify the hobby a bit and even give you some ways to get started if you’re interested. I’d really like to interview a professional in the space in the future to get some more targeted guidance, so hopefully that comes together.
I’m not sure how active the comment section will be on this post about cigars, but for those who do smoke I’m curious about what you’re into these days. But perhaps more importantly (advance warning, vulnerability will be required here) I am also curious to hear about hobbies or interests that you’ve had to learn how to enjoy on your own terms despite how others might feel about it.
Being able to hit the gym after work has become my default "me time" and a space I feel comfortable in. Changing into my gym-fit and getting into a different headspace is huge with the work that I do. I throw a podcast on or some tunes, depending on my mood, and 9 times out of 10 I leave feeling better or at least not as wrapped up in my thoughts from the work day. Yes, being able to see results is nice but at this point, it's become my "beer after work", if you will, and love that intangible feeling/vibe after a good workout.
I think I’m one of those people that sent you a DM haha. But going to a good local shop was the best advice. I still only smoke about twice a year, but I have a profile I towards for those cherished nights. I am thinking of getting some nice cigarillos. Finding an hour can be tough but a nice 20 minutes could be a great reset.