Dear Playboy Advisor: Questions From Men and Women to the Advice Column of Playboy Magazine (7 page)

Are Cubans that great?

Are Cuban cigars all they are said to be? I have found a place that sells Cubans and I wonder if I should switch from my current brand.—G.G., Atlanta, Georgia

The quality of Cubans has declined in recent years, and some smokers say they were never that great. Joel Sherman, author of
Nat Sherman’s Passion for Cigars
, notes that Cuban cigars are usually rushed to market because they’re in such demand. “When you take a puff on most Cubans, you feel a burning sensation in your chest—testimony to the high ammonia content due to lack of proper aging,” he writes. “Back in the 1950s, like a lot of smokers, I clenched my teeth and grinned through the experience of smoking a Havana. They had to be good, right? It took
an almost macho disregard for comfort to smoke one all the way down.” Expect to pay $25 to $50 each for handrolled Cubans, which have been contraband in the U.S. since a trade embargo was enacted in 1963. Cohibas are the Cubans of choice, but it’s often difficult to tell if you’re holding the real thing. A third to a fourth of so-called Cubans are phonies. How can you spot a fake? Sherman suggests checking each cigar because “boxes of Cubans are notoriously inconsistent in color.” And if you don’t feel that burn, you’re probably not smoking what you paid for.

What is the penalty if you’re caught sneaking Cubans into the U.S.?—H.B., Akron, Ohio

If you are smuggling a box or two, a friendly U.S. agent will seize them. (Customs says it incinerates about 240,000 Cubans each year.) If you’re a serious smuggler with a suitcase, you’ll face jail time and/or a hefty fine. Keep in mind that you don’t have to visit Cuba to lose your stash—the ban applies to Cubans purchased anywhere in the world. You can challenge a seizure, but don’t expect much. A Philadelphia man who lost 100 cigars purchased in Havana took the government to court, arguing that because he had purchased the cigars on the black market, he hadn’t enriched the Castro government and thus didn’t violate the embargo. A federal judge congratulated the cigar lover for his “quite attractive” argument, then ruled in favor of the government. In 2004 the Treasury Department Office of Foreign Assets Control tightened its regulations of Cuban cigars, ruling that it’s illegal for Americans to buy or smoke them anywhere in the world.

Should you remove the band?

Should you remove the band before smoking a cigar?—A.H., Pittsburgh, Pennsylvania

Keep the band on, for several reasons. First and foremost, removing it can damage the wrapper. Richard Carleton Hacker, author of the
Ultimate Cigar Book
, finds that the band also is a good reference point for where to hold the cigar (in Victorian times, the band kept the fingers of a gentleman’s glove from becoming stained with tobacco, or with the powder used to give cheaper cigars a uniform color). The band is also a way to announce your allegiance. As Hacker says, you wouldn’t buy a sports car and rip the emblem off, so why do it with your fine cigars? That attitude doesn’t play well overseas (where the band is always removed), but Hacker observes that European cigar smokers, especially
the French and English, are hypocrites. “They claim that leaving the band on a cigar is ostentatious,” he says. “So what they do is carefully place the band faceup in the ashtray, where everyone can see it.”

The proper cut

Is there any way to open a cigar if you don’t have a cutter handy?—H.T., Peoria, Illinois

Many smokers in the Caribbean and Central America have never used a cutter. Instead they incise with their thumbnail around the head of the cigar, then remove the cap. If you don’t have experience with this technique, it’s best to save it for emergencies because it’s easy to muck up. We prefer cutters; they contribute to the ritual and showmanship of lighting cigars, and that’s half the reason we smoke them. We also aren’t keen on sticking a thumbnail into the same leaf that’s about to go into our mouth.

You write that you like cutters because they “contribute to the ritual and showmanship of lighting cigars.” What a crock of elitist crap. Over the years I have used various cutters (V-cut, guillotine, bore, etc.) but have never found anything better than the one used by millions of smokers: their teeth.—F.U., San Francisco, California

You can bait us, but we’re not biting.

Best way to beat a runner

What’s the best way to get rid of the runner in a cigar?—P.R., Philadelphia, Pennsylvania

When a cigar burns faster on one side than the other, it’s generally a lost cause. Tunneling occurs because of poor fermentation of the leaf, a natural flaw in the cigar or improper rolling. You can try to recut above the run, but a cigar that has already been lit never tastes as good the second time around.

Thanks to a technique I learned from the good people at De La Concha Tobacconist in New York City, a tunnel can be recovered. Lick your thumb and wet the length of the cigar several times from the tip of the run to the end of the cigar. In many cases, this will slow down the rate of burn behind the tunnel, and allow the opposite side to “catch up.” It doesn’t work on every run, but it’s worth a try.—P.L., New York, New York

Several readers asked why you can’t repair a runner by holding your lighter under the slower-burning side. The technique sounds simple but never works because typically the flaw continues for the entire length of the cigar. That explains why the De La Concha method gets the job done—sometimes.

How far should you go?

I was at a party when the host invited us to smoke cigars on the porch. Everyone had a different opinion about how long a cigar should be smoked. That is, do you continue until you hit the band, or until you can’t hold it any longer? Also, how much of the tip should be cut off?—S.H., Allen, Texas

If you’re smoking a great cigar, you can continue until your facial hair bursts into flames. So says Richard Carleton Hacker: “Some people stop when they hit the band,” he notes. “Others take the band off, which I don’t recommend because it provides a good place to hold the cigar and lets others know what you’re smoking. Every cigar burns differently and has a characteristic taste, but they all tend to get a little more rank as you get closer to the end and have less tobacco to filter the smoke. It’s not unusual for many cigars to begin smoking poorly halfway through.” As for the head, slice it from the top, just as the tip starts to curve outward.

COLLEGE LIFE

Let’s party.

Reach out and touch someone

A college friend invited me to come along on a weekend boat trip. I grabbed my bikini and we drove to a lake in a van with four guys she knew. When we arrived, there were about 30 boats tied together on the water. After about two hours, a guy grabbed a bullhorn and announced it was time for Raise the Flag. Everyone climbed over the boats to a stage that was built from two pontoons. Four guys volunteered to have strings tied around their waists with flags that draped down over their crotches. They also had their hands tied behind their backs. Four girls then climbed onstage and paired off with the guys. The women yanked down the guys’ swim trunks and were handed bottles of oil to rub on themselves and anywhere on their partners except their cocks and balls. Prizes were awarded each time a flag was raised. Two guys also won $100 when they allowed the women to measure their erections. The game continued on various boats. My girlfriend had a tape measure, so we both got our hands on a few penises. At one point I watched the guys bring my friend to orgasm with their hands, and I found myself getting very turned on. I touched only one guy, and he was the only guy who touched me. We’ve talked on the phone a few times since, and now I’m torn between going on the next trip and wanting to be with him. Any suggestions?—A.R., Oklahoma City, Oklahoma

God bless America—after all that, you ask the Advisor a relationship question? We need a moment to calm ourselves. Ask this guy out, already. Getting to know him better is the only way to determine if you should pledge your allegiance, or if he wants it. At the very least, you’ll have a chance to raise his flag in a sovereign state—your bedroom.

The stray hair

One afternoon my roommate’s girlfriend came into our dorm room when my roommate wasn’t around. She started paging through one of our copies of
Playboy
. She commented on how beautiful the Playmate was and then unfolded the centerfold. That’s when it happened. A strand of pubic hair fell out. She looked at me and said, “I see you like her too!” I turned beet red and didn’t know what to say. Now when we see each other, she teases me about it. Thankfully, she has a heart and never says anything when others are around. Should I try to discuss it with her? I haven’t mentioned the
M
word, but she knows what’s going on.—L.A., Los Angeles, California

A strand of hair proves nothing. Demand a DNA test! It looked like a chest hair to us! You were framed! Okay, the situation doesn’t look good, but here’s some news: Your roommate’s girlfriend masturbates. Your roommate masturbates. Everyone in your dorm masturbates. It’s normal. Being aroused by the image of a beautiful, nude woman is normal too. So your friend is ribbing you for being normal. She’s playing with you and that’s cool—we like her sense of humor and discretion.

My room is a sex hut

Last semester I transferred to a new college. I have yet to find my niche, so I spend a lot of time in my room. At least five times a week my roommate’s girlfriend comes over and they fool around. I sit outside until they’re finished. Other times she shows up in the middle of the night and they wake me up with their love vibrations. I don’t feel comfortable saying anything because my roommate doesn’t say anything when I smoke pot in the room. What should I do?—A.S., Oneonta, New York

Your roommate is not going to curtail his sex life on the suspicion that it bugs you. Make it official. Tell him you don’t want to be a cockblocker but that your grades and sleep are suffering. Ask if he’d be willing to limit his girlfriend’s visits to two weeknights and one on the weekend, during which time you’ll make yourself scarce (you’re doing that anyway, so it’s a good negotiating position). If he hesitates, offer to keep your reefer unlit when he’s around. While compromise is grand, the more important point is that you need to get off your ass. Find a few girlfriends so you can kick your roommate out once in a while.

So many girls, so little time

A buddy and I live in a coed dorm and both have girlfriends. About three weeks ago two girls who live upstairs came down to visit. Soon the talk turned dirty enough for us to joke about getting naked, and weird enough that these girls did. They must have planned the encounter because they took turns on us. Afterward nothing was said except that it was great and they shouldn’t tell our girlfriends. Now our upstairs friends are visiting three or four times a week, always late at night. We can’t keep this up because there’s too much pressure to perform well for them and our girlfriends. Also, we’re not getting enough sleep and our grades are suffering. I’m afraid if we tell the girls to stop coming they’ll rat on us. What should we do?—T.S., East Lansing, Michigan

Isn’t this half the reason you went to college? If you’re tired, lock your door twice a week, and don’t answer.

Analyze this

I’m a 28-year-old graduate student who most people would judge to be handsome. Earlier this year, I began noticing a gorgeous student from another department. We seemed to keep similar schedules, and I would often see her in the library or the cafeteria. We have never met, but for a long time we exchanged semiflirtatious smiles and glances. Often, I would look up and catch her staring at me, and then she would quickly look away. Many times she caught me doing the same. A few times we passed on campus and said hello. After several months of this, I waited for the right moment to introduce myself. Then something strange happened: For no reason that I can discern, the smiles and glances stopped. I have a clear vibe about this: If she’s aware of my presence, or if she spots me on the street, she makes an effort not to look my way. Naturally, I take this as a bad sign, but some of my friends think her new body language might be good news. Perhaps she feels rejected because I didn’t talk to her when I had a window of opportunity. Or maybe she’s interested but just nervous. Obviously, she’s aware of my presence. Then again, maybe she just thinks I’m a creep and hopes I’ll get lost. Is there any way to tell these things before I walk up to her and risk making a fool of myself?—J.M., Boston, Massachusetts