First things first: It’s okay to admit you don’t know jack about cigars. In fact, that may be the best way to guarantee you won’t show up with some stale old sticks (you know: the ignorance of arrogance, and so forth). Second step: Head to a cigar store. And by cigar store, we don’t mean some local bodega that carries a few Black & Milds behind the counter. We mean a real cigar store—somewhere that specializes in tobacco products, and has proper humidification technology.
More than brand or country of origin, proper humidification may be the most important factor when buying a cigar, which is why you need to go to a reputable outlet—if it’s stored within the ideal humidity-level window (65-75%, just FYI), your chance of getting something decent to smoke skyrockets. Too low, and the sticks will be dry and crackly. Too high, and they may feel spongy (they also may prove difficult to keep lit). You can also tell quite a bit from the construction of a cigar—the leaf it’s wrapped in should be mostly smooth, and generally not too vein-y.
Aside from that, it comes down to personal taste. Do you prefer something mild or spicy? Want a fat gauge (a cigar with some girth) or something thinner? How long do you want the cigar to burn for? Decide on these factors, and then let the store clerk be your guide.
When buying for a group, it may be difficult to indulge the peculiarities of everyone’s palate. According to Mark Grossich, owner and operator of the Carnegie Club, a cigar lounge in NYC, you should “recognize that some may not be regular cigar smokers, so bringing a cigar that everyone can enjoy—such as a medium-bodied cigar—would be best.” Mark’s medium-bodied favorites include Alec Bradley Black Market, AVO #2, and Davidoff 2000. These three can be found at TampaHumidor.com and FamousSmoke.com.
Rafi Kohan has written for GQ, Details, ESPN.com, and the Wall Street Journal, among others. He recently started a monthly cigar-and-scotch club. In his words: “It's like book club, but drunker.”