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Playboy Advisor on Sexbots, Weed and the Etiquette of Asking Out a Waitress


Question: What is the etiquette for asking a waitress or bartender out when she's working? Some of the places I frequent have very attractive servers, but I don't want to be distasteful and put them on the spot.—J.L., Scottsdale, Arizona

Advisor: The etiquette is you don't. Of course there's the occasional exception to that rule (a friend of ours once closed a bar with a hot bartender and took her home, but he looks like a young Tom Cruise and is guilelessly charming and a gentleman of the highest order). But we've heard many more stories from waitresses complaining about douchey male patrons hitting on them. Many a good dinner has been ruined by the ice-cold dessert of rejection. Of course those attractive servers are dating and they're often dating other servers, bartenders and chefs. If you're determined to date someone in the food and beverage industry, you might consider changing careers.


Q: How close are scientists to creating a real sexbot?—R.S., Toms River, New Jersey

Advisor: If you mean a walking, talking, sex-obsessed fembot à la Austin Powers, not close at all. The sex robot is one of those futurist fantasies that, like the flying car, have captured the imagination but have so far failed to materialize. In the next few decades we could see the convergence of, say, a sexy Siri and an extremely dexterous, ambulatory android, but today's offerings are a far cry from that reality. True Companion makes a $6,995 silicone-covered product that responds to touch, has motorized private parts and is capable of rudimentary conversation. But if you're dead set on experiencing sex with minimal emotional attachment, a better use of your $6,995 would be to avail yourself of an elite member of the world's oldest profession. Better yet, you could spend it on psychotherapy and figure out how to overcome your fear of intimacy.

Q: I've long been fascinated with time capsules and have finally decided to make one. Among the objects I'd like to include in my capsule is a bottle of some sort of alcohol. It will be buried in a remote location in the Texas Panhandle and so will be there a long time, possibly 100 years or more, until someone has the opportunity to discover and open it. What would be the best kind of alcohol to bury? I'm thinking some brand of whiskey or a bottle of a good red wine.—H.G., Canyon, Texas

Advisor: With the exception of the best sweet wines, such as French Sauternes, very few wines will be drinkable after 100 years, even when stored in a climate-controlled wine cellar. Given the extreme temperature fluctuations in the Texas Panhandle, we recommend going with an 80-proof spirit. It will never freeze (unless the temperature drops to minus 30 degrees Fahrenheit). Whiskey is a great idea—particularly high-end Kentucky bourbons, which are currently in short supply (collectors are buying and hoarding them at unprecedented rates). Plus, should you find yourself in a tight spot financially, you'll be able to break open your time capsule and cash out your liquid assets.


Q: What color deck shoes would you recommend to wear with black pants? Can you suggest a particular style?—T.H., Cambridge, Massachusetts

Advisor: When pairing pants with shoes of any style you generally want some contrast in shade. Pale tan or camel looks nice against black, whereas a dark brown would look too similar in tone and thus seem a bit like an accidental mismatch. With a casual look you can play more with the contrast. Top-Siders, the Sperry-branded version of the classic boat shoe, come in dozens of styles and colors. If your personal style is more flamboyant, push the contrast to the maximum with red or white shoes. Or revert to the "like with like" (i.e., monochromatic) rule of fashion and wear black Top-Siders. Get a pair with white soles so the bottom half of your body doesn't completely disappear.


Q: Every time I go to bed my wife of eight years checks my computer and cell phone. She sits there for hours looking through every single action I've taken. I've tried password protection, but that caused a problem. I'm not doing anything wrong, but I feel like a prisoner in my own home. When I confront her about this, we always start to argue and she wants to know what I'm hiding that she can't see. What's going on here?—T.C., Birmingham, Alabama

Advisor: The fact that you describe your attempts to discuss your wife's monitoring of your activities as "confronting her" leads us to believe you're behaving defensively, as does the fact that you tried to lock her out. Soften your approach and open up more. If you truly have nothing to hide, then ask her to tell you specifically what she's worried about: What are her concrete fears? Was there a past breach of trust, whether actual or perceived? Sometimes a small suspicion or insecurity can grow into something bigger than is warranted. If it's all in her head, then you should take the focus off you and empathize with her; whatever is in her mind is obviously causing her at least as much mental anguish as it is you. Let your digital life be an open book to her and take steps to figure out what is causing her anxiety. If letting her open up while remaining open to hearing her fears doesn't help, couples therapy would be a safe place to explore this together.


Q: My friends say I pay too much for my glasses—$600 a pair versus two pairs for $120. I'm convinced my eye doctor uses a better lens material than the discount places. Is there a difference? Also, what is the make and model of the sunglasses John Elway wore at the Super Bowl?—L.K., Salem, Ohio

Advisor: The biggest difference is the business model: Discount eyeglass stores are built on value, volume and vanity. As much as stylish glasses can improve your look, that's not as important as how they improve your looking. In a 2011 study, researchers ordered a total of 200 pairs of glasses from the top 10 online discount-eyeglass companies and discovered that in some cases prescriptions were incorrect, special coatings weren't applied and, most alarming, nearly 25 percent of the glasses included lenses that failed impact testing. Glasses are much more than a functional fashion statement; they're medical devices, and an optometrist puts that as the priority. As cool as it is to virtually "try on" glasses on a fancy website to see how the frames fit your face, an optometrist is trained to make sure the frames are positioned to best improve your vision. This can be done only in person. As for John Elway's glasses, if you're talking about the wraparound shades with the gold trim, our best guess is they're a slightly older style of Prada shield glasses.


Q: My wife and I have been together for more than 15 years. She has no interest in having sex with me anymore. In the past the sex has been good and we enjoyed playing with various toys and vibrators, but I recently discovered she has been using our favorite vibrator alone. She got really angry when I discovered this and she refused to discuss it. The next day she packed up the vibrator in question and put it away as if it were evil. Why does being discovered upset her? And why is she going it alone? I didn't disapprove of what she was doing other than the fact that I felt left out. In fact I'm pleased that she wanted any sex at all, even if it was by herself. She gets upset if I ever "go solo," so I stopped for years. But out of sheer frustration I have started again, this time in secret, which I'm uncomfortable with. What do you say?—N.M., London, Ohio

Advisor: We suggest telling her everything you just told us. But before you do, ask yourself what the issue is with going at it alone, which is by no means abnormal, particularly in a relationship as long as yours. You sound a lot like the couple in "The Piña Colada Song" (anyone younger than 40 should google the lyrics), who over the years have grown out of touch with each other's dreams and needs. It sounds as though you and your wife are both adept at self-love. Admit why you've drifted apart, commit to remedying the situation and then work on rekindling your desire to be intimate together. Maybe the first step is to join self-loving forces and compare notes.


Q: Now that pot is legal in Washington state, I'm considering using it for medicinal and possibly recreational purposes. I have trouble with insomnia, and I can no longer take sleeping pills because of the adverse effect they have on me. Marijuana is said to help with sleeplessness, so I'm going to give it a shot. Here is the problem: I have two kids, and my wife hates smoking of any kind. I've started to look into vaporizers, but I'm kind of lost when it comes to deciding which to go with. Can you give me any advice on tackling this? The smaller the device the better—I don't want to have to explain a new appliance to my kids.—H.R., Seattle, Washington

Advisor: While marijuana can certainly be used to treat insomnia, for some people it can have negative effects. Some respond to it as they would a stimulant. Others find it increases their anxiety. Others don't like the mental fog the next day. Before you invest in a pricey vaporizer, talk to a reputable doctor about dosages and strains. (It sounds as though you've tried marijuana before, but be warned: Weed is more powerful than ever these days.) You'll know soon enough if it's right for you. If it turns out it is, buying your own weed and grinding it for vaping allows you more freedom with choosing strains. Since you have kids, don't let anyone talk you into buying edible marijuana candies, cookies or other sweets. That's an accident waiting to happen. The Pax model from Ploom is a quality vaporizer that's only about four inches long, has a sleek, low-key design and is rechargeable.


Q: Several porn videos I've seen show couples having anal sex and then switching to vaginal sex. Do they stop filming and clean up to make the switch, or are they taking a risk here? Isn't it unwise to go from anal to vaginal? Also, in some other videos a man may lick a woman's anus—without using any protection—and then lick her vagina. I'm surprised they wouldn't take some sort of precaution. Isn't this risky behavior as well?—S.S., Englewood, Colorado

Advisor: Porn videos are shot over hours, with multiple takes and much resting and washing and lunch breaks and hair and makeup adjustments and water breaks and fluffing and a lot of other boring stuff that civilians don't have to bother with while having sex. But practicing sexual hygiene is one way the porn industry stays in business, and it's the one thing you should emulate, even though you don't have the benefit of editing your sex-position changes into one seamless narrative. Yes, it is absolutely risky to go straight from anal to vaginal or oral sex without either washing your penis thoroughly with soap and hot water or changing condoms.


Q: For the past few months I've noticed my typical morning wood has turned into a raging, all-night-long hard-on. It actually wakes me up in the middle of the night. That may not sound like much of a problem, but it seems to be the only time I get hard. Strip joints, online porn and even regular sex with my wife don't seem to do much. Is this a physical or a mental problem?—M.P., Chicago, Illinois

Advisor: The medical term for what you describe is "nocturnal penile tumescence." It's used by sex therapists as the primary test to determine whether the reasons for erectile dysfunction are psychological or physical. Clearly your hardware is up to snuff. Tackle this problem by seeing a sex therapist who can help you get your two heads in sync again.


Q: How long is it okay to keep a cigar outside of a humidor before lighting it up? Is there a better way to preserve it than a ziplock bag?—M.C., Wichita, Kansas

Advisor: Ideally less than an hour, as a cigar instantly begins to lose moisture in a dry climate. Immediately transferring a cigar to a metal tube can buy you a day of freshness. You can also buy cigars from a smoke shop in factory-sealed glass tubes. All of these are elegant and effective alternatives to the plastic sandwich bag. If you're going on a trip, you can get a decent dopp-kit-size travel humidor for around 30 bucks.


Q: First of all, I'm not the guy who wrote in about a threesome in the December issue. However, I have had several threesomes and I'm an average guy. The first was 15 years ago when I was a freshman in college. The last was with the love of my life, my wife of 10 years, and a lady we met at a bar while on vacation. All I can say is, almost everyone is curious and nobody wants it to be weird. Take a deep breath, enjoy all the bits and pieces and never bring it up after the fact. After our threesome, my wife and I actually began to feel like some modern-day Bonnie and Clyde.—T.M., Montauk, New York

Advisor: Unlike Bonnie and Clyde's, may your luck never run out. Thanks for the report from the front lines.


Q: My husband and I were high school sweethearts and have been together now for more than a decade. We have always had (and still have) a healthy and satisfying sex life and are both comfortable expressing our fantasies. Although he is the only sexual partner I've ever had, he was pretty experienced when we met. Until recently I'd never met anyone else for whom I felt the same sexual attraction I do for my husband. However, a few months ago I started having intense fantasies about one of my husband's friends. I'm mortified. I can't bear to say anything to my husband. I love him so much and he never disappoints me sexually, but I just can't stop thinking about his friend. Is there something wrong with me? How can I get these fantasies to stop? We see this friend often and I'm wondering if I should be avoiding him.—M.M., -Muncie, Indiana

Advisor: There is nothing wrong with you at all. Studies show that anywhere between 60 and 80 percent of women fantasize about men who aren't their partners. So don't beat yourself up. However, obsessive fantasies often provide a handy escape from real-life challenges. Do an honest inventory of your feelings: Are your career, family life and social life as satisfying as your sex life with your husband? Is the rest of your marriage what you want it to be? If all that's in order, we suggest channeling the bonus arousal into your sex life with your husband. The fantasies will most likely diminish with time. You haven't told us anything about how your husband's friend is behaving. If he's flirting with you or has any part in encouraging your attraction, we'd suggest keeping some distance until either he gets the message or your fantasies subside. The last thing you want to do is jeopardize the great thing you and your husband have built.


Illustration by Skip Sterling who you can also find on Twitter and Tumblr.

If you have a question for the Playboy Advisor relating to food and drink, fashion and taste, or sex and dating, e-mail The most interesting questions will appear in an upcoming issue of Playboy. And to read every Playboy Advisor ever, visit our complete archive at

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