How to not be a douchebag: Outdoor kiosk edition

There we were, sitting in the open-air piazza at Regina Pizzeria during the St. Anthony's feast in the North end of Boston at the end of August. 

Know why this picture is so good?
Because Valentino took it.

We'd ordered our two favorite pies (We're creatures of habit.) and had a lovely view of alllllll the people milling by and our old friends Rolling Stogies and their lovely sticks while consuming as many slices of pizza as two people can handle and not die.*

Our seats were the perfect vantage point to watch people who have never smoked a cigar choose one and then fumble around, trying to figure out what to do next. We would have gotten up and offered assistance, because we're nice like that, but we didn't because 1. We waited in line for half an hour for those seats and we were going to sit in them until we were forcably removed or melted by glaring stares of other people waiting in line; and 2. Pizza.

Here's what we saw, as the next generation of cigar smokers tried to impress friends and girlfriends. We had the sad and did much head shaking. 

If you want to look like a suave, experienced cigar smoker, please learn from their mistakes.

Step 1: Consult your friends and say the names of the few cigars you've heard of. Ask if the proprietor has those.  
What you should do: Right now, go to a local cigar shop or lounge, and ask the proprietor for recommendations; be sure to tell him** you're a novice. He will not judge you. He will welcome you. Take pictures of the bands and keep them in your phone, as well as make note of some of the names. No one will know you're you're using a cheat sheet when you approach the cigar kiosk with your friends. 

Step 1.5: Mention that you wouldn't mind buying a Cuban if he has any. 
What you should do: Don't ask. Even if he did have them, which he doesn't, he wouldn't sell them to you. 

Step 1.75: Dodge laser beams of hate radiating from proprietor's eyes. 
What you should do: Not have to worry about it, because you didn't ask.

Step 2: Ignore what the proprietor says because that cigar band over there looks cool. (No judgements; I buy books because they have cool covers.)
What you should do: Listen to the person speaking to you. He is an expert, or at least more of an expert than you are. Respect his knowledge. His goal is to sell you something you're going to like so you come back for more. 

Step 3: Select one cigar randomly and ask "Is this a good one?"
What you should do: Just like with food, everyone has their own taste. What Valentino loves, you might not because of the strength or taste or nicotine level. That doesn't make the cigar bad--just not right for you. So is it a good one? Yes--selling junk would hurt the shop's reputation. As for the Rolling Stogies, they only have premium cigars, so yes, they're all "good ones."

Step 4: Ignore proprietor again because your friend makes an uneducated suggestion. 
What you should do: Unless your friend has experience with cigars, you probably want to ignore him and listen to the person who knows what he's talking about. Probably a good suggestion across the board. 

"We're professionals. We're here to help!"

Step 5: Ask how much it is. 
What you should do: A valid question, of course. Usually, prices are marked.  If price is a concern, you might want to say when you first start chatting, "I'm looking for something in the $8 range." 

Step 6: When you're told the price, say, "What? For one? That's ridiculous. Forget it, man."
What you should do: If you are shocked, balk silently so as to not embarrass yourself in front of your friends. Please. It's the least you can do. Cigar smokers do not quibble over prices. You're paying for a hand-rolled product. Don't be a cheap bastard.  

Step 7: Have a dumbfounded look on your face when they ask if you'd like it cut straight, V, or punched. 
What you should do: For the love of all that is good and holy, do not suggest biting the end off. If you're not sure, default to straight. This will make smoking a bit easier. When you get some experience, you can experiment with different cuts. 

Step 7.5: Say you'll cut it and then when you're handed the cutter, slide the cutter about half an inch. 
What you should do: You have two choices here. 1. Hand the cigar to the proprietor when he offers and watch how he does it so you know for next time. Or: 2. Snip a teeny bit, and when we say teeny, we mean about one-sixteenth of an inch. According to Cigar Aficionado, a bad cut will ruin a cigar, so it's probably best, in this casual setting where distractions abound, to leave it to the professional. 

Step 8: Ask for matches and then try to light a cigar with said matches. 
What you should do: Unfortunately for you and the cigar, lighting a cigar with matches is difficult in general but definitely in this wind. We know you want to do it old school, but reject the challenge and use the proprietor's torch lighter he has at the ready.  If you're inside, go for it, but outside...meh. Your friends are only going to wait so long.

That's Mike (the Rolling Stogies owner), a good student,
and a slew of onlookers getting schooled.
Why is this weirdly blurry, you ask?
Sigh. Photography by Penny

Step 9: Puff once or twice because you saw someone on TV do that, feel satisfied and smug and walk away cockily. Realize twenty feet away that the cigar is out. 
What you should do: Lighting a cigar is a process that can't be rushed, like toasting a marshmallow, according to Cigar Aficionado. If your friends won't wait for you to complete the process because they light their cigs in a nanosecond, tell them you'll catch up with them. Otherwise you're going to be stuck with a dead stick pronto. 

Step 10: Hold your cigar with two fingers (pointer and thumb) while looking at the sky. Inhale. Raise your arm towards the sky and the arc it down like you're rowing a canoe. Blow the smoke straight up like you're a human smokestack. 
What you should do: Not that. Since we can't be there, we're going to suggest at this point, watch how the guys in the Rolling Stogies tent are smoking their cigars. 



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So there you have it. We want you to look like a classy dude (or dudette). We want you to be the one folks look up to! We can help! Stick with us and we'll get you there!!



*Actually, Valentino saved a teeny tiny bit of room because our friend Omar was across the way shucking clams for immediate consumption as well. Then there was an arancini with my name on it too. It's always a big food day. Wheeeeee!

**Or her, obviously, but the he/she thing will clutter the writing.