At some point, every man hears the seductive call of the cigar, beckoning him into a mysterious world of whiskey-drinking, business-talking and relationship-griping. Sometimes it’s your co-workers or friends who convince you to light one up and “join them on the patio”. Sometimes it’s your father or grandfather. But whatever the circumstances, if you choose to embrace the stogie, there are a few pointers you should be aware of so that you don’t come off looking like this guy:

Awkward Cigar Smoker

Whether you’re a seasoned pro, or a cigar virgin, here are 10 tips to help you smoke your cigar like a boss.

1. Sniff It

Smelling a cigar-1

In general, if you like the smell of the cigar, you’re gonna like the flavor of the tobacco when smoking it. When choosing at the store, run it under your sniffer to get a rough idea of the taste. A great entry-level cigar is the Monte Cristo White, made with Dominican tobacco and a Connecticut wrapper, with a creamy, mild taste. If it’s 7am and you’re playing golf, consider the Monte Cristo for your breakfast cigar.

2. Snip It 

cigar guillotine

To quote Vince Vaughn from Wedding Crashers, “Let’s play a little game called Just the Tip.” At the rounded end of the cigar, you’ll see a tiny dark line encircling it. This is the cigar’s “cap”, the edge of the main leaf that wraps up the binder and tobacco. If you cut below this line, it’s like cutting the belt that holds the cigar’s pants up. When you get near the end of your smoke, the whole cigar is gonna fall apart and flare out, looking like Elmer Fudd’s shotgun. You want to make your cut somewhere between the belt and the tip.

3. Toast It

Toasting REDUCED - Brian Potter Video:FLICKR-1

Brian Potter Video/FLICKR

Don’t light your cigar by placing it directly into the flame. Instead, you want to “toast” it, rolling the foot end near the fire without touching. Think of it like roasting a marshmallow: if it catches flame, you’ve gone too far. What’s the issue? You risk charring the tobacco and drawing that black smoke up through the length of the cigar, perverting the flavor. It’s not the worst thing that can happen, it won’t ruin your experience — just like an all-black marshmallow can still be pretty tasty – but you want to avoid it if you can. Slowly heat your cigar over the flame while rolling. Then work in your draw, pulling the hot air up through the tobacco until the foot of the cigar begins to glow a warm, welcoming orange.

4. Don’t Torch It

Torching  - Jesse CourteManche FLICKR-1

Jesse CourteManche/FLICKR

Torch lighters are all the rage these days, mostly because they’re windproof and extremely convenient. But there is also a growing sentiment that butane isn’t totally “clean” and burns too hot, making it more likely for your cigar to catch fire. So what’s the alternative? Good old-fashioned matches. As long as the wind isn’t your enemy that night, they’ll burn awhile, especially if you use 2 or 3 bundled together. And if you really want to get fancy, light the cedar sticks that are included at the bottom of most cigars boxes, then use them to light your cigar. Boss level: 10.

5. Rock The Boat

Trey Matula/FLICKR

Trey Matula/FLICKR

Sometimes you get a nice, circular orange glow on your first toasting. But other times, you get a disproportionate light and you “boat” it. That’s when only one small part of the foot is lit, maybe the edge, or a small section in the middle, burning black, ruining your every puff. In this case, turn the cigar slowly, blowing on the lit end, as you attempt to “push” the embers and heat across to the other side. Be careful not to draw too hard if you boated it, as you’ll only pull the narrow flame deep into the cigar, creating a burning-elevator shaft type of situation that only Bruce Willis could escape from. Another trick if you boat it is to simply stop and let the cigar rest in the ashtray. The embers will eventually make their way sideways across the cigar until you have a nice, even glow.

6. Don’t Worry About How You Hold It

Daniel Zedda/FLICKR

Daniel Zedda/FLICKR

Find a position that’s comfortable for you and quickly accept that everyone is different. From Churchill, who chomped it, to Bill Clinton, who, uh, made love to it, every man holds his cigar in his own way. You can encircle it like a pool cue, pinch it like a joint, or go with the classic wedge between two fingers. It’s all about comfort.

7. Pair It

craft beer and stogie-1

It really doesn’t matter with what. Cigar smoke goes well with almost anything. But a great rule of thumb is to match the lightness or heaviness of the beverage with the lightness or heaviness of the cigar. Pair it with whiskey, scotch and bourbon of course. But also a lot of craft beers go well with a cigar, like an imperial with a higher alcohol content on a night when you’re not gonna knock back a six pack.

8. Take Your Time

Turkish PM Turgut Ozal's wfie Semra -Prometheus72 :


Many cigar newbies (present company included) make the mistake of thinking it’s a cigarette, puffing away until they are the first man to cross the finish line. But your average cigar is going to last 45 minutes at least. It’s something you ease into and draw once every 30 seconds to a minute or so. Take your time. Enjoy a few laughs. Also, you don’t have to ash it constantly like a cigarette, either. Instead, wait until your ash is about an inch long and then gently tap it off into a tray.

9. Let It Sit

Cigar in ashtray

It’s okay to take a break and let the cigar sit for a minute or two… if you have a nice orange glow burning, it will stay lit. And if it ever goes out, the best practice really is to cut it and toast it again, lighting your little stubby.

10. Once You’re Ready, Splurge         

Justin Cigar Pic

J. Capozzi

As a rule of thumb, the cigar industry is accurately priced. You pay for the good stuff. Not that you can’t find great cigars for $5, but once you reach some higher price points, jumping up to $12 then to $30, you’re going to start hitting some complex flavors that are truly special. A nice step up from entry level is Liga Privada #9 from Drew estates, a manufacturer that always makes quality cigars. Liga Privada means “private blend” and was created for the sole smoking pleasure of Drew Estate President Steve Saka. It’s a great “next level” cigar as you climb the ladder to Churchill and Castro level. Bear in mind that the cigar industry is just getting abused by pricing right now. Legislators are attacking the tobacco industry and cigars are getting folded into that. They’re not cigarettes, but they’re getting penalized as such. So prepare to start spending more and more on your newfound habit.


Cigar smoking guy Cool -1

Whether you’re a seasoned pro or a cigar virgin, there are a few tips you should always keep in mind. Toasting the cigar so the foot doesn’t char, taking your time and not racing to the end and starting with milder flavors before working your way up will all help make for a smooth experience. But the most important thing about any cigar smoking session is the company you keep. If you choose to light one by yourself, it makes for an excellent time of self-reflection. More often than not, though, you’ll be sharing the experience with people who mean something to you, friends, family. And therein lies the real draw: lighting one up with the people you are closest with, as you take a break from work, kids and marriage to indulge in exotic tobaccos, smooth whiskeys and good conversation.

About The Author

Michael Berman

Husband and father of two who works as a professional writer, having sold screenplays to Sony, Disney, MGM and Showtime among others. Always on the look out for solid, useful information to share with other parents on

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