Cigar 101: How to Smoke a Cigar Without Becoming "That Cigar Guy"

I enjoy cigars.

Not because they make me feel sophisticated. If you've met me for more than about five minutes, you've probably figured out that's not really my lane.

A few years back I had a membership at one of the cigar lounges over in San Antonio. Beautiful place. Big leather chairs that looked like they belonged in an old library. Dark wood everywhere. Lockers full of cigars. A humidor that could've doubled as somebody's first apartment. Great selection. Good people.

But if I'm being honest...

It never really felt like me.

I'd walk in wearing what I always wear—a hat, jeans, boots, and a t-shirt—and every now and then I'd catch one of those sideways looks. You know the one. Nobody says anything because cigar people are generally pretty polite, but you can almost hear somebody thinking, "Well... this oughta be interesting."

Did it stop me from going?

Not for a second.

The cigars were still good.

The conversations were still worth having.

But it did get me thinking that somewhere along the line cigars picked up this strange reputation that they belong to a certain kind of person. Like you're supposed to know all the terminology before you're allowed to enjoy one. Like there's an unwritten dress code. Like if you don't own a torch lighter that costs more than your first truck payment, you're somehow doing it wrong.

I don't buy that.

A cigar is one of the least pretentious things ever made.

Think about it for a minute. It's tobacco. Somebody grew it. Somebody fermented it. Somebody rolled it by hand. Somebody packed it into a box. And eventually it found its way into your hands because you wanted to sit still for an hour with a good drink and some good company.

That's it.

The cigar never asked you to wear a sport coat.

The cigar never asked you to memorize wrapper varieties.

The cigar never demanded you describe it as having "subtle notes of saddle leather, toasted almond, and the faint aroma of rain falling on a Guatemalan hillside."

People did that.

The cigar just wanted to be smoked.

That thought came back around last week during Ciders & Cigars over at Hill Country Cider House.

Overholt helped with the event, and watching people pick up their first cigar was probably my favorite part of the evening. You could almost see the questions forming before they asked them.

"Am I cutting this right?"

"Is this lighter okay?"

"How hard am I supposed to puff on this thing?"

"Why's that guy staring at his cigar after he lit it?"

Good questions.

Questions everybody has the first time.

The funny part is that most of us only know the answers because somebody else showed us once. Nobody came out of the womb knowing how much of the cap to cut off a cigar. Somewhere along the line, somebody handed us a cutter, showed us the width of a dime, and said, "Don't cut any farther than that."

That's how most good hobbies work.

Somebody teaches you just enough to get started, then gets out of the way.

That's what this is.

Not a master class.

Not a certification.

Not an attempt to turn you into the guy who corrects strangers at the cigar shop.

Just enough information to help you enjoy a good cigar and, maybe more importantly, help the next guy enjoy his first one.

Start With a Cigar That Fits the Afternoon

One of the first things I noticed after spending more time around cigar shops was that new cigar smokers almost always gravitated toward the biggest cigar in the humidor. I understood the logic because I almost fell into the same trap. You're spending good money, so your brain starts doing math. More cigar must mean more value. Bigger has to be better. It makes sense right up until you realize a Churchill isn't "better" than a Robusto any more than a one-ton pickup is better than an old Jeep. They're just built for different jobs.

That's really what size affects more than anything else—time.

A Churchill might stay with you for an hour and a half if you're smoking it the way it was intended. A Robusto may be closer to forty-five minutes. A Toro lands somewhere in between. None of those sizes are right or wrong. The mistake is buying the cigar you think you're supposed to smoke instead of the cigar that fits the amount of time you actually have.

I've watched guys spend the last third of a cigar checking their watch every two minutes because they realized they were running late. At that point the cigar isn't relaxing anymore. It's become another thing on your schedule that you're trying to finish before moving on to the next thing.

That's backwards.

One of the reasons I enjoy cigars so much is because they refuse to be rushed. You can certainly try, but they'll remind you pretty quickly that tobacco doesn't like being hurried. Smoke too fast and the cigar gets hot. Once it gets hot, it starts getting bitter, and then people decide they bought a bad cigar when really they were just asking it to do something it wasn't made to do.

Buy the cigar that fits the afternoon you've actually got, not the one you wish you had. If you've only got forty-five minutes after dinner before heading home, smoke the Robusto and enjoy every minute of it. If you've got a Saturday afternoon with nowhere to be, then maybe that's the day for the Churchill.

The cigar isn't keeping score.

Before You Ever Reach for the Cutter

Before I cut a cigar, I almost always spend ten or fifteen seconds just looking it over. Not because I'm trying to inspect it like a jeweler looking at a diamond, but because tobacco is an agricultural product. It's leaves. Every cigar is a little different, and sometimes they'll tell you something before you ever light them.

I usually roll it gently between my fingers first. It should feel firm, but it shouldn't feel like you're squeezing a wooden dowel. At the same time, you don't want it feeling soft or mushy either. You're looking for just a little give, the kind that tells you the cigar has been stored properly and is probably going to smoke the way it was intended.

While I'm holding it, I'll glance over the wrapper. Little veins don't bother me. Tobacco leaves are supposed to look like leaves. But if I see a big crack or a section that's already peeling away before I've even cut it, I'd rather know that now than halfway through the smoke.

Then I'll give it a smell.

This is usually where cigar conversations take a hard left turn into poetry.

You'll hear somebody talk about toasted almonds, saddle leather, cedar from a specific mountain range, hints of espresso, dried cherries, black pepper, cocoa, and probably the emotional state of the farmer who grew it.

Good for them.

Most of the time I just think, "That smells like good tobacco."

Sometimes I notice cedar. Sometimes coffee. Sometimes pepper. Sometimes it's just rich tobacco and that's enough.

You don't have to identify seventeen tasting notes before you're allowed to enjoy a cigar. You're not taking a test. You're making sure the cigar smells clean, feels right in your hand, and makes you want to light it.

That's really all you're after.

Cutting the Cigar Is Easier Than People Make It

If there's one moment where I can almost guarantee a new cigar smoker starts overthinking things, it's right before they make the cut.

Everybody suddenly gets nervous.

"What if I cut too much off?"

"What if I ruin it?"

"What if everybody notices?"

First of all... nobody's paying that much attention to you. They're worried about whether they're doing something wrong.

Second, cutting a cigar isn't nearly as complicated as the internet would have you believe.

All you're trying to do is open the head of the cigar enough that air can move through it while leaving enough of the cap intact to hold everything together. That's it. There isn't a secret technique passed down from generation to generation. You're just making a clean cut.

For years I've used the same little rule because it's easy to remember. With a straight guillotine cutter, cut about the width of a dime from the end of the cigar. That's usually enough to open it up without getting into trouble. Go much farther than that and you risk cutting into the shoulder of the cigar, which can let the wrapper start unraveling. It's not the end of the world if it happens, but it's certainly not the way you want to begin a good smoke.

These days I probably reach for a V-cutter more often than anything else. I like the draw it gives me, and I think it keeps the cap together a little better, especially on larger ring gauges. Plenty of people feel the same way. Plenty of other people don't. That's one of the things you'll discover about cigars. There are a lot of opinions floating around, and most of them aren't important enough to argue over.

Punch cutters have their place too. Some guys love them because they're quick and clean. Personally, I think they're a nice option, but if somebody asked me what to buy for their very first cutter, I'd still hand them a straight cutter or a V-cutter and tell them not to overthink it.

The cutter matters a whole lot less than making one clean, confident cut.

Before You Light It, Take One Puff

This is one of those little habits somebody showed me years ago, and I've never stopped doing it.

Before you ever strike a lighter, take a cold draw.

That's all it is. Put the cigar in your mouth and take a slow pull through it while it's still unlit.

Part of what you're checking is the draw itself. You want a little resistance, but not so much that it feels like you're trying to drink a milkshake through one of those tiny coffee stirrers. If the cigar feels plugged before you light it, chances are it isn't going to magically fix itself once fire gets involved.

The other reason I like a cold draw is because it gives you your first little introduction to the cigar. Sometimes you'll notice a bit of sweetness. Sometimes cedar. Sometimes pepper. Sometimes it just tastes like tobacco, and that's perfectly alright too.

Not everything has to be an experience.

Sometimes it's just a good cigar.

Fire Isn't the Goal. An Even Light Is.

When I first started smoking cigars, I was terrible at lighting them.

I'd stick a torch right into the foot of the cigar like I was trying to weld the thing together, puff on it three or four times as fast as I could, and then spend the next twenty minutes wondering why it tasted bitter.

Turns out tobacco doesn't appreciate being introduced to a flamethrower.

These days I take my time.

I hold the flame just below the foot of the cigar and slowly rotate it without actually touching the tobacco with the flame. You're not trying to light it yet. You're toasting it. You're warming the tobacco evenly so the entire foot has a chance to catch at about the same time.

Think about lighting charcoal instead of paper.

Once the foot is toasted, then I'll bring the cigar to my mouth and take a few slow draws while continuing to rotate it. Usually that's all it takes.

The goal isn't to get the cigar lit as fast as possible.

The goal is to get it lit evenly.

Those are two very different things.

A lot of people ask whether they should use a butane torch or a soft flame. I've used both, and I don't think either one automatically makes you a better cigar smoker. A torch is great when the Texas wind decides it wants to be involved. A soft flame works beautifully on a calm evening. What matters far more than the lighter is your patience.

I've watched people ruin perfectly good cigars with expensive lighters simply because they were in a hurry.

I've also watched somebody light a cigar beautifully with an ordinary Bic because they understood that fire isn't the point.

An even burn is.

The Funny Thing About Ash

I've always gotten a kick out of how much attention people give cigar ash.

Somewhere along the line, somebody decided the length of your ash was a measure of...well...something. I've never quite figured out what. Toughness maybe? Skill? Patience? I don't know. Whatever it is, you'll eventually run into the guy who's trying to carry three inches of ash around like he's transporting nitroglycerin because he heard that's what "real" cigar smokers do.

I wouldn't worry about it.

A good ash can tell you something. If it's holding together nicely, chances are you've got a well-rolled cigar that's burning the way it should. That's one of the little clues people learn after smoking for a while, and it's worth paying attention to. But like most things in the cigar world, people have a way of taking a perfectly useful observation and turning it into a competition.

Gravity eventually wins every time.

When the ash starts looking like it's ready to let go, tap it gently into the ashtray and keep enjoying your cigar. Don't smack it against the side of the ashtray like you're trying to knock mud off your boots. You're smoking a hand-rolled cigar, not putting out a cigarette behind a gas station.

The funny thing is, once you stop worrying about the ash, you start noticing the things that actually matter. Is the cigar burning evenly? Is it getting too hot? Are you enjoying it? Those are much better questions.

Slow Down. The Cigar Isn't Going Anywhere.

I think this is the mistake I made more than any other when I was getting started.

I'd light a cigar, get into a conversation, and before I realized it I was puffing on the thing every twenty or thirty seconds. It wasn't because I was trying to. I was just treating it like...well...every other distraction in modern life. Hurry up, keep it going, don't let there be any dead air.

Cigars don't work that way.

The faster you smoke them, the hotter they get. The hotter they get, the rougher they taste. Then people blame the cigar when, most of the time, the cigar didn't do anything wrong.

It reminds me a little of cast iron. Everybody wants to know the secret, and the secret is usually just...quit messing with it so much.

Take a puff.

Set it down.

Take a drink.

Listen to the conversation instead of thinking about what you're going to say next.

Watch the fire for a minute.

There's no prize for finishing first. In fact, finishing first is usually a pretty good sign you're doing it wrong.

One of the reasons I've come to enjoy cigars as much as I have is because they force me to operate at a speed I probably should have been moving all along. The cigar doesn't care how many emails I have waiting or whether my phone buzzed in my pocket. It just keeps burning at its own pace, quietly reminding me that not everything worth doing has to be done quickly.

I could probably stand to be reminded of that more often than I'd like to admit.

The Band, the Drink, and Knowing When You're Done

People ask all the time when they're supposed to take the band off. My answer is usually, "Whenever it wants to come off."

Leave it alone for a little while. As the cigar warms up, the glue softens and the band will usually slide right off without any drama. Try to peel it off too early and every once in a while you'll pull part of the wrapper with it, which is a great way to spend the rest of your smoke wishing you'd waited another five minutes.

As for what to drink with a cigar, people love making rules.

Whiskey gets all the headlines, and for good reason. A good bourbon and a good cigar have been friends for a long time. Coffee is hard to beat, especially on a cool morning. Last week reminded me how well a dry cider works too. The apple cuts through some of the richness without getting into a shouting match with the cigar, and after watching people at Ciders & Cigars try that combination for the first time, I don't think it'll be the last time we see it.

Honestly, though, drink what you enjoy.

Just do yourself one favor if you're new to cigars...

Eat something first.

Trust me on that one.

And when should you stop smoking it?

That's probably the easiest question in this whole article.

When it quits tasting good to you.

Not when somebody else tells you it's time. Not when you've smoked it down to the point you're burning your fingertips because you "paid for the whole cigar." Somewhere along the last third you'll know. The flavors change, the smoke gets warmer, and eventually the cigar tells you it's had enough.

Listen to it.

Set it in the ashtray and let it go out on its own.

Don't Become That Cigar Guy

If you've spent any amount of time around hobbies, you already know this guy.

He exists everywhere.

He's into coffee, but somehow can't let you enjoy yours because your grinder wasn't calibrated to the nearest micron. He likes whiskey, but before you've had your first sip he's already explaining why the bottle you bought isn't the right bottle. Give him five minutes around pocket knives and he'll have you convinced opening an Amazon box requires a degree in metallurgy.

Cigars have that guy too.

The funny thing is, I don't think he starts out that way. I think he genuinely falls in love with the hobby, learns a lot, and somewhere along the road forgets what it felt like to be the new guy standing in front of the humidor wondering which cigar to buy.

Don't lose that.

Learn everything you can. Learn where tobacco comes from. Learn why different wrappers taste different. Learn how to cut one cleanly, light it patiently, and appreciate the amount of work that went into putting that cigar in your hand.

Then use what you've learned to make somebody else's first cigar a little less intimidating.

That's how traditions stay alive.

Not because somebody guarded the gate.

Because somebody held it open.

And if, years from now, somebody asks you how to smoke a cigar, I hope you don't start by trying to impress them.

I hope you hand them a cutter, point to the cap, smile, and say, "About the width of a dime."

Because that's exactly how most of us learned.