If you've been meaning to get into cigars but feel a little intimidated by the cigar room, the lingo and the regulars in the leather chairs, you could be picking out your own cigar, lighting it properly and chatting easily with the tobacconist within the next 30 days.
Because this system teaches you one small piece at a time, and has you smoke one cigar a week alongside it,
you learn the way regulars learned: by doing it, not by memorising a textbook.
Here's the thing nobody tells you. Almost every cigar lover you admire was once standing in that same doorway, staring at a wall of boxes in the walk-in humidor (the climate-controlled room where cigars are kept), quietly hoping nobody would ask them a question. The difference is that most of them had a friend, an uncle or a patient tobacconist to show them the ropes. The Regular is that friend, in your pocket.
And it's just $12, about the price of one good cigar. So please keep reading.
Anyone can feel at home in a cigar lounge (even if you've never smoked a single cigar!)
Becoming "Cigar Shop Ready" requires NO:
- ✕No expensive humidor or fancy gear on day one
- ✕No years of smoking experience
- ✕No memorising hundreds of brands
- ✕No "refined palate" (you'll build one as you go)
- ✕No pricey cigars to learn on
- ✕No cigar-smoking friend to hold your hand
- ✕No pretending you know more than you do
- ✕No awkward silence when a regular asks what you're smoking
Here's how it works:
Read One Short Lesson
Each week, open one part of the 30-Day Playbook. It's short, written in plain English, and covers exactly what you need for that week and nothing more.
Smoke One Guided Cigar
Pick up the week's cigar (we tell you what style to look for, starting mild), smoke it at a relaxed pace, and fill in a page of your Tasting Journal as you go.
Take It to the Shop
Bring your "Talk Like a Regular" Cheat Sheet, ask the questions we give you, and try out what you've learned in real conversation. A little more each week.
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Four weeks. Four lessons. Four cigars. By the end, you'll know the words, the rituals and your own taste, and you'll walk into the shop like you belong there. Because you will.
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Why this works (when YouTube rabbit holes don't)
Most beginners try to learn cigars by watching random videos and reading forum threads. The result? Information overload, conflicting advice, and still no idea what to actually say when the tobacconist asks, "What are you in the mood for?"
The Regular works differently, for three simple reasons:
What's Included?
✓ The 30-Day Playbook (PDF + online lessons)
Your step-by-step guide in 4 weekly parts:
- Week 1: Your First Cigar. The anatomy of a cigar (the cap, the foot, the wrapper, the binder and filler, all explained simply), the essential lingo, and how to buy and smoke your very first one: how to cut it, toast it (gently warm the end before lighting), light it, why you don't inhale, and how to pace yourself so it stays enjoyable.
- Week 2: Reading the Menu. Wrappers (the outer leaf that gives a cigar much of its look and flavour), the main tobacco countries, the difference between strength (how much it hits you) and body (how rich and full the flavour feels), shapes and sizes, and how to read a cigar band or a shop menu without squinting.
- Week 3: Lounge & Shop Etiquette. How to talk to the tobacconist (the shop's resident expert), easy conversation starters with regulars, and the small things not to say or do so you never feel out of place.
- Week 4: Making It Yours. Storage basics (what a humidor is and why humidity matters), pairing cigars with drinks, and figuring out "your" style and how to describe what you like so the shop can point you to cigars you'll love.
✓ "Talk Like a Regular" Cheat Sheet
The essential terms in plain English, conversation starters, smart questions to ask, and the newbie mistakes to avoid. Printable, or keep it on your phone for a quick glance before you walk in.
✓ The 4-Cigar Tasting Journal
Guided tasting pages, one for the cigar you smoke each week, moving from mild to medium. Learn to notice flavours (cedar, coffee, cocoa, pepper, cream) and put them into words.
Bonus
✓ The Cigar Matchmaker
An interactive online quiz. Answer 6 questions and in about 2 minutes you'll get 5 beginner-friendly cigars matched to your taste and budget, plus exactly what to ask at the shop.
Bonus
✓ The Whiskey & Cigar Pairing App
Our free companion app for iPhone puts a pairing guide in your pocket. Pick a whiskey or a cigar, and it suggests matches based on flavor profile.
Just $12
One payment. Everything above, instantly. About the price of one good cigar.
Get The Regular for $12 →Here's what your first 30 days look like after joining:
- Today. You take the Cigar Matchmaker quiz with a coffee in hand. Two minutes later you've got 5 beginner-friendly cigars matched to your taste and budget, and a few things to ask at the shop. For the first time, you've got a plan.
- End of Week 1. You've read the first lesson. You walk into the shop, ask for a mild cigar by name, and the tobacconist nods. You cut it, toast the foot, light it slowly, and remember not to inhale. You take your time. You fill in your first journal page: "creamy, a little nutty, smooth." Not bad for a first-timer.
- End of Week 2. You can read a cigar band. You know what "Connecticut wrapper" (a light, mellow outer leaf) and "medium-bodied" mean. When the menu lists a Nicaraguan cigar, you actually know what that tells you.
- End of Week 3. You're back at the lounge. A regular asks what you're smoking. Instead of freezing, you tell him, ask what he's enjoying lately, and before you know it you're twenty minutes into a good conversation.
- End of Week 4. You know how to keep a few cigars fresh at home, what to pour alongside them, and how to describe what you like. You walk up to the counter and say, "I've been enjoying medium-bodied cigars with a bit of spice, what would you suggest?" And you mean it.
This is what's possible when you learn one step at a time, with a guide by your side. And you can start today.
Don't do this alone
No standing frozen in the humidor — The Cigar Matchmaker and Week 1 lesson tell you exactly what to look for and what to ask for.
No botched cuts or harsh, over-puffed smokes — The Playbook walks you through cutting, toasting, lighting and pacing, step by step.
No nodding along to words you don't understand — The "Talk Like a Regular" Cheat Sheet translates the lingo into plain English.
No etiquette slip-ups — Week 3 covers the unwritten rules of the shop and lounge, so you're welcomed rather than tolerated.
No "I don't know, it tastes like... cigar?" — The Tasting Journal teaches you to notice and describe flavours, so you can finally say what you like.
Frequently Asked Questions
"I've literally never smoked a cigar. Is this too advanced for me?"
Not at all. This was built for complete first-timers. Week 1 starts with what a cigar actually is and walks you through your very first one, from buying it to the last relaxed puff.
"Do I need to buy a humidor or special equipment first?"
No. To start, you just need a cigar, a simple cutter and a lighter or matches (the Playbook explains which to get). Storage basics come in Week 4, once you know whether you want to keep cigars at home.
"How much will the cigars cost me?"
That's up to you. The guided cigars start mild and are chosen to be beginner-friendly, and the Cigar Matchmaker factors in your budget when it suggests options. You don't need expensive cigars to learn.
"How much time does this take each week?"
Each lesson is short, a comfortable read with a drink in hand. The rest of your week's "homework" is enjoying one cigar and filling in a journal page. Most of the time you'll spend on this is time you'd enjoy anyway.
"What if I can't keep up with one cigar a week?"
The 30 days is a guide, not a rule. You keep lifetime access, so go at whatever pace suits you. The lessons and journal will be there when you're ready.
"Will I really feel confident at the shop after this?"
You'll have the knowledge, the words and the experience of four guided cigars, which is more than most beginners ever get. Confidence comes from doing it a few times, and the whole program is built to get you doing exactly that, with the guarantee below backing you if it doesn't feel right.
"Is this for anyone?"
It's for adults of legal smoking age only. Cigars are meant to be savoured slowly, not inhaled, and the Playbook teaches exactly that.
The real cost of waiting
At $12, the money isn't the hard part. The bigger cost of waiting is another month of walking past the shop, or walking in, mumbling "just looking," and walking out again.
Here's your choice:
Option 1
Join today for $12. Read Week 1 tonight, smoke your first guided cigar this weekend, and spend the next 30 days becoming the person who knows their way around a lounge.
Option 2
Keep putting off something you've wanted to enjoy for a while now, and keep guessing at the counter.
The Playbook is ready. The leather chair is waiting.
The Investment
One payment · lifetime access
- ✓The 30-Day Playbook (PDF + online lessons, 4 weekly parts)
- ✓"Talk Like a Regular" Cheat Sheet
- ✓The 4-Cigar Tasting Journal
- ✓BONUS: The Cigar Matchmaker quiz
- ✓BONUS: The Whiskey & Cigar Pairing app (iPhone, free)
All delivered instantly. One payment. No monthly fees. No subscription.
Get Instant Access →My "Keep Everything" 30-Day Guarantee
Here's the deal: I want you to try The Regular completely risk-free.
Get instant access. Read the Playbook. Take the Cigar Matchmaker quiz. Print the Cheat Sheet. Smoke your guided cigars and fill in your Tasting Journal. Go to the shop and try it all out.
If at any point in the next 30 days you decide it isn't for you, for any reason or for no reason at all, just send me an email and I'll refund every penny.
No questions asked. No hoops to jump through. No awkward back-and-forth.
And here's the best part: you keep everything.
That's right. Keep the Playbook. Keep the Cheat Sheet. Keep your Tasting Journal and your Matchmaker results. Keep everything you've learned.
Why would I do this?
Because I'm confident this works. I know that once you've smoked your first cigar the right way, held a real conversation with a regular, and heard yourself describe a cigar you enjoyed, you won't want your $12 back. You'll want your next cigar.
I'd rather take on 100% of the risk myself than have you sitting on the fence wondering "what if?"
So here's what this means:
You're not risking $12. You're not risking anything. You're simply deciding whether you want a friendly, step-by-step guide to feeling at home in any cigar shop.
If it doesn't work for you, you get your money back AND you keep everything.
That's as fair as I can possibly make it.
One Last Thing
You don't need to figure this out alone.
You don't need to sit through hours of videos, decode forum arguments, or quietly hope nobody in the lounge notices you're new.
You don't need to keep putting it off because you're not sure where to start.
The Regular gives you everything in one place: a 4-week Playbook, a Cheat Sheet for the lingo, a Tasting Journal for your first four cigars, and the Cigar Matchmaker to tell you what to buy. Built for first-timers who want to enjoy cigars properly, and feel welcome doing it.
This month could be the month you finally pull up a chair, light up properly and join the conversation.
Or it could be another month of "one day I'll get into cigars."
It's just $12. The Playbook is ready. And with the 30-day "Keep Everything" guarantee, you simply cannot lose.
Just $12 · 30-day "Keep Everything" guarantee