How To Choose Your First Cigar


how to choose (4)

Smoking cigars is one of life’s simple pleasures in my book, along with sex with a gorgeous girl, or a hearty laugh with your close friends. If you’ve never had a cigar, but you’re curious about it, then this blog post is for you. If you’re an experienced smoker, then this might be a fond trip down memory lane. If you find cigar smokers pretentious, then you probably think it’s too ‘try-hard’ to have threesomes as well and prefer tofu to prime rib. No worries, this article isn’t for you then. It’s for the men genuinely interested in trying out a cigar for the first time.

The most common excuse I’ve heard from guys who haven’t smoked a cigar yet, is that they’re slightly intimidated by how to get started. I’ll clear something up for you right now: follow these practical and simple steps and you’ll do just fine. It’s easy to get overwhelmed by all the different cuts, brands, etc, but if you just have a desire to try it out, then you’ll be fine.

I’m not an expert, but I’ve learned a thing or two in my almost 9 years of smoking them and I’ll share it with you now in a step-by-step format.

  • Step 1 Do’s and Don’ts
  • Step 2 What To Pay For Your First Cigar
  • Step 3 Tips On Selecting A Cigar
  • Step 4 How To Cut A Cigar
  • Step 5 How To Light A Cigar
  • Step 6 How To Smoke A Cigar
  • Step 7 Where To Smoke Your Cigar

Let’s get started gentlemen…

Step 1 Do’s and Don’ts


  • Go into a reputable cigar shop (Pro-Tip: use the app ‘WhereToSmoke’ to find lounges and cigar shops, More on that later in the article), be cool and tell them “I’ve never smoked a cigar before. What are your suggestions?”. Cigar smokers tend to be very helpful in giving a newbie smoker suggestions, plus, lets not forget they want you to have a good experience so you keep spending money there.
  • Smoke your first cigar somewhere cool. Don’t buy one and smoke it in your car, or stand on the Promenade in Santa Monica puffing away while getting screeched at by the SoCal anti-smoking ‘nazis’. Cigar smoking is as much about the experience as it is the tobacco. There’s a reason why cigar lounges are generally cool to hang out in. It’s all about the experience. A rooftop in a major city as the sun sets is a great location as well, or on the beach while watching whales flirt with the shore. I’ve done both and it’s a close call which is the better experience.


  • Buy a cigar from a gas station, Starvin’ Marvin’, or Flying J truck stop. These cigars aren’t stored properly in a humidor, so the taste will be shit and when you unwrap it, it’ll probably crumble quicker than a soggy Oreo. Your Uncle Leon might suggest it, but this time he’s wrong.
  • Don’t chew the end of the cigar off to smoke it. Maybe you saw a pic with Winston Churchill doing that, but don’t. There is a way to remove the cap without cutting it, but for right now use a cut, otherwise you’ll probably ruin the cigar. Later in the article I share a video explaining how to properly cut it.


Smoking cigars with your male friends is a great way to do business and bond. 

Step 2 What To Pay For Your First Cigar

One of the biggest misconceptions about cigar smoking from non-smokers (besides telling us we’re all dying from cancer after one cigar), is that you have to drop a ton of cash for great cigars.

You don’t.

As you progress with becoming a cigar aficionado (if you choose to), then sure, you’ll probably increase the quality of cigars you smoke and drop more cash, but with your new-found friends at your local cigar shop you’ll also find out about good deals and it all balances out.

You can get a good entry-level cigar for around $6-10.

If you absolutely hate it after trying it you won’t be pissed you spent more.

Pro-Tip: unless you absolutely abhor the first puff of your first cigar, I’d highly suggest trying 3 different cigars. The type of cigar, flavor and experience you have plays a big part of whether it’s something you enjoy or not.

No different then if your first time having sex was a bad experience. It doesn’t mean sex sucks and it doesn’t mean you’ll never have a great experience, just try a different girl cigar. 🙂


In the humidor of a great little cigar shop by San Diego.

Step 3 Tips On Selecting A Cigar

Most newbie cigar articles will point you in the direction of the type of cigar the writer THINKS you might like, while adding in some affiliate links to online cigar shops. While there’s nothing wrong with specific suggestions and affiliate links, it doesn’t serve the reader very well, because what I like, you might detest. Instead, my tips are based on helping you select a cigar in the shop along with the help of one of the employees so you get something that is right for YOU.

The first tip is selecting whether you want a mild to full-bodied cigar.

The general rule of thumb is always start with a mild and this usually holds true, however, if you’re a regular cigarette smoker you might find that a mild is just that: too mild.

Here’s my suggestion: select one of each.

A mild, a medium bodied and a full-bodied. At the price point I mentioned before this is a low investment and then you can switch from cigar to cigar to see which one you like most. For example, you’d start with the mild. Say after smoking it for a minute or two you decide it’s not strong enough. No worries. Try the medium-bodied and so forth. That way you can find out quickly which one works best for you at little cost.

To make this simple think of it like this:

Mild: lighter smoke

Medium: heartier and more flavorful

Full: stronger smoke, richer in flavor (usually) and sometimes spicier

A mild-bodied cigar does not mean it’s mild in flavor necessarily, because it comes down to the actual blend; it’s about the strength of the cigar.

I remember one of my early cigar smoking experiences, a mentor of mine handed me a full-bodied cigar. After a couple of puffs I thought my chest was going to collapse because it was too much for me. I switched to a mild and enjoyed that one immensely. Now I enjoy medium-bodied with the occasional full-bodied cigar.

To recap: find a good cigar shop, go in and say you’d like to select three cigars. A mild, a medium-bodied and full-bodied and state your price range. If they’re good people, they’ll ask you a couple of more specific questions that only you can answer based on your individual preferences of what you think you’ll like, then make some helpful suggestions. It’s not rocket science and the more honest you are with them about how you’re new to the cigar world, the more they’ll help you.

Step 4 How To Cut A Cigar

Here’s the deal about cutting a cigar: you will make some bad cuts. It’s inevitable. Too many drinks, a pretty girl gliding by with endless legs distracting you as you make the cut, or laughing at a joke your buddy just told you can all mess it up. Don’t trip. Have some patience and don’t be hard on yourself. Here’s a video explaining how to make the perfect cut by the fine people over at Cigar Aficionado magazine, but if you’re still confused, just have them cut your cigars before you leave the shop, or have the waitress cut it at the lounge.

Step 5 How To Light A Cigar

Light the cigar by slowly turning it keeping the flame on the edge. Don’t torch it and be patient. You’re not lighting a cig. It’s a different dynamic. If you just put it in your mouth and try lighting it like a cigarette you’ll find it lights uneven and you’ll get a retarded looking cigar and an uneven smoke. You also want to be aware that WHAT you light it with makes a difference. Your trusty Bic you bought from the gas station for $.99? Don’t use it to light a cigar. Here’s a video that outlines it very well because some things are better explained by watching a pro do it:

Step 6 How To Smoke A Cigar

I highly recommend trying your first cigar on a FULL stomach. Smoking cigars on an empty stomach (especially your first one) could lead to you feeling queasy. There’s a reason many cigar lounges offer appetizers and even full course meals of which smokers will consume first before lighting up, although some enjoy their cigar while eating. The latter is my preference.

Don’t suck on it like a wench in a club bathroom stall sucking off the hot promoter she just met.

I’ve seen newbies do this and I gently point it out so they can avoid embarrassment. It ain’t a nipple on that broad you used to bang.


Here’s a hilarious clip of Arnold mocking Jimmy Fallon the first time he smoked at the Grand Havana Room NYC. Arnold’s depiction of Jimmy trying to puff on it is exactly what you want to avoid. Start at the 2 minute mark to skip the irrelevant portion of the clip.

Step 7 Where To Smoke Your Cigar

My go-to app, especially when traveling, is called ‘WhereToSmoke’ and you can find this free resource in the app store. It calculates your location and shows you the closest smoke shops and lounges.

WhereToSmoke desktop edition here.

As promised earlier in the post, here’s a couple of cigar lounge suggestions I have for those of you based on the West Coast, or East Coast that are my personal favorites.

The Beverly Hills Grand Havana Room is a private membership based cigar lounge based in BH of course and also NYC. Now you might be thinking, “Well Christian, why would you suggest a private cigar lounge?” and the answer is simple. Get your network up (or conversely tap into your existing network) and you’ll find someone connected to it. Members range from Arnold himself, to Robert De Niro, to high-profile doctors, lawyers and businessmen. Make that link and you’ll not only enjoy a great cigar lounge by being invited there by an existing member, but you’ll also make some great connections inside. Win-win.


It’s much bigger than it looks in this picture and even has an outside massive deck for dining and smoking.

Here’s the humidor which is quite the sight to behold in person.

In NYC there’s a cigar lounge called The Carnegie Club, which is open to everyone. I went there for the first time a couple of weeks ago with my fellow members of Baron Society and it was truly a great experience. From the ‘Sinatra’ singer to the accompanying live band it was top-notch. You can find out more about them here.


Some of my best memories have been surrounded by friends and oftentimes business associates, smoking cigars and having a great conversation. The biggest business deals I’ve ever cut? Always in a cigar lounge. There’s a lesson in there somewhere.

Lastly, everyone always asks, “Are Cuban cigars really that good?” and the answer is a resounding “yes”. I’ve been smoking them since well before POTUS just touched down in Cuba (get a Cuban friend if you don’t have one yet). Smoking one IN Cuba is on the Travel To Do List, along with a big booty Cuban girl. Both will be great experiences, but who knows which will be the best.

Enjoy your first cigar smoking experience and welcome to the club.

Pro-Tip: To really enhance your first smoking experience, set a personal or business milestone, then after achieving it, go have your first cigar. Thank me later.

Tap into the playboy lifestyle here.

Read More: How To Wake Up Like The Rich and Powerful

6 Replies to “How To Choose Your First Cigar”

  1. Ahhh the memories …. I’ve been traveling all over south America, and surprisingly they have a pretty shitty cigar scene. I am actually having a buddy who owns a cigar shop send me a care package with a great mix and a 40 year old Padron as a reward for a race I am running. Love the article, can’t wait to get another cigar now


  2. Hey Christian,

    Just wanted to say I’m a big fan and thank you for another kick ass article. I’ve learned a lot from your teachings and am thoroughly enjoying the journey to becoming the best man I can be. Thanks again!



  3. One thing you forgot to mention that might seem obvious is you don’t actually inhale the smoke into your lungs. You simply hold the smoke in your mouth or retrohale by blowing it out through your nose for enhanced taste.

    A great compliment to a cigar is a fine glass of scotch, wine, port or beer. Many cigar lounges will recommend pairings for your cigar. The cigar flavor can completely change with a drink and vice versa.


    1. Didn’t forget. Assumed everyone knew about inhaling etc.
      Good addition with the drinks comment. That could be an entirely different post though due to how far down the rabbit hole one goes.


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