5 questions to ask on a date

By Ayren Jackson-Cannady

Early date chit-chat can become so formulaic that you walk away knowing little more about a person than a few résumé-ready bullet points: Where he grew up, where she went to school, for whom he toils to get his biweekly paycheck. “We tend to ask more questions about a car or house than about the person we are going out with and potentially entrusting our hearts with,” says Eve Hogan, author of Intellectual Foreplay: Questions for Lovers and Lovers-to-Be. That’s not to say your early get-togethers should be interrogation-quality, with the blinding light bulb, two-way mirror and good-cop/bad-cop act. The trick is to ask questions that aren’t too personal, but still reveal your date’s tastes and his or her values. What’s the difference? Well, if you like Joni Mitchell and your date digs Ice-T, you may assume you’re not a match (different tastes)—unless you can discern that you’re both compelled by politically-minded lyrics (similar values). So next time you’ve got silence to fill, ask one of these playful and engaging questions.

1. What’s your favorite scene from your favorite book or movie? Talking about mass media and pop culture can clue you in to similar interests and worldviews. “Books, movies, and music all transmit powerful messages of hope or emotion,” says Hogan. “If you have radically different preferences, there may be some fundamental differences between the way the two of you look at the world.” But asking your date to name his or her favorite scene can help you distill what’s important to him or her beyond just genre.

2. What do you love about your job? The standard, “What do you do?” is a closed question that doesn’t reveal much about a person other than a job title. But if you phrase the career question a bit differently, you can delve into your date’s likes and dislikes; reveal his or her strengths; see how he or she handles conflict; and find out how happy this person is with life overall. Think about the different impressions you’ll form if your date answers the question, “Knowing that I’m helping people fulfill their dream” versus “Deciding what to order for lunch!”

3. What’s your definition of a relationship? Granted, it takes a bit of build-up to ask this question (usually, once you begin discussing your dating histories, you can slip this one in), but it’s worth asking. Does your date want to be wined and dined, or are you both looking for a 50/50 relationship? It’s too soon to know what this specific potential relationship will look like, but a question like this lets you share your expectations and fundamental beliefs. “I like to ask this question early on, because I’ve found that some women I’ve dated didn’t know what they wanted out of our relationship,” says Mario Webb of Ft. Walton Beach, FL. “They came into it just hoping things work out without telling me what they expect. Needless to say, things haven’t worked out.” And if your date’s answer is outside the range of what you consider acceptable, you’ve saved yourself future heartbreak by finding out before you fall for him or her.

4. If money were no object, what would you do with your life? This tried-and-true icebreaker showcases your date’s hopes, dreams, and even regrets—topics that often remain untouched by even serious romantic partners. The answers can range from a desire to travel to going back to school to learning how to play the violin. Two buttoned-up stockbrokers might discover they both share a secret longing to be athletes or a shared devotion to public service. Your date’s response will help clue you in to common goals and interests that go beyond what you do on a day-to-day basis.

5. Will you share an embarrassing moment with me? This fun question is great to ask when a date has gotten a little tense or quiet, because it reveals both details of your date’s history and his or her character. Just know that you may have to share an awkward experience first in order to make your date feel comfortable. “One of the great things is that our humanity is a bonding thing,” says Hogan. “Our ability to laugh at ourselves is critical in a budding relationship.” So make it clear that you’re not looking for dirt on that plagiarism incident in 11th grade, but rather something goofy, like the time you drove a golf cart into the water, installed a chandelier upside-down and so forth.

By asking these questions and considering the answers, you’ll gain valuable insights onto your date—and know whether the two of you are likely to click on future get-togethers.

Ayren Jackson-Cannady has written for Quick and Simple, Time Out New York, and Suede.

6 secret guy turn-ons

By Matt Schneiderman

Sure, girlie-girl moves — a hair flip here, an eye batted there — will attract a guy... some of the time. But you may be surprised at the things guys really can’t resist about women, and some of them are the very qualities women fear will drive men away—from letting a curse word loose to leaving all kinds of makeup near his bathroom sink. Here’s why these habits and others actually win a man over.

1. He loves that you indulge at dinnertime. Guys love girls who love to eat—not girls who say they aren’t hungry and then pick at their date’s food all night. Paul, 30, who lives in Boston, thinks that food may be the reason he fell in love with his fiancée: “When we first started dating, I thought it might be awkward if I wanted greasy food like wings—I figured she’d think it was fattening or unhealthy. Women I’d dated in the past only wanted to go out for salad or sushi. But she was enthusiastic about eating all kinds of things with me. I loved that easygoing attitude of hers.” Aside from showing that you’re not high-maintenance or neurotic about your weight, that kind of unabashed enthusiasm also tends to translate into other areas—including the bedroom. “A woman with a healthy appetite for food tends to have a healthy appetite on all levels, and sex is absolutely a part of that,” explains Barton Goldsmith, Ph.D., author of Emotional Fitness for Couples: 10 Minutes a Day to a Better Relationship.

2. He loves your occasional obscenities. You may worry that it’s not ladylike, but occasionally letting a curse escape your lips at an unexpected moment can be a major turn-on. “Hearing a woman use profanity out of context gives a guy a shock of sexual adrenaline,” explains Ian Kerner, Ph.D., author of She Comes First: The Thinking Man’s Guide to Pleasuring a Woman and co-host of Discovery Health’s Love on the Rocks. “Men like women who can be tough and assertive, and as long as she doesn’t take the talk too far, it’s a positive thing.”

3. He loves that you aren’t a neat freak. Believe it or not, guys find the proliferation of hair products, accessories and unidentified stuff strewn about your apartment oddly sexy. “I love that my wife makes a bigger mess than I do,” says Ziad, 31, of Durham, NC. “When she cooks, food ends up all over the place. It shows that she’s carefree, and it reminds me to enjoy the moment rather than worrying about the consequences.” This laid-back mind-set also carries over into your weekend wardrobe. “Guys love a woman who’s not trying too hard,” explains Dr. Kerner. “Most men think a pair of boxer shorts and a ratty old T-shirt around the house is your sexiest look.” So don’t spend hours choosing the perfect date-night outfit or getting your place in House Beautiful–shape, because men love you just as you are—in your comfortable, slightly sloppy glory.

4. He loves your extra padding. Sure, you’ve heard that men love women with curves, but how about those extra pounds you’ve been trying to sweat off at the gym? There’s a good chance that your guy loves them, too. Just ask 26-year-old Nick: “My girlfriend exercises regularly, but I think the little pudginess in her thighs is sexy because it shows she’s not perfect.” Sure, your extra padding may make men feel a little better about their own beer bellies, but there’s also a biological reason why men like this. Psychologists at the University of TX determined that men were most attracted to women with hourglass figures — specifically, women whose waists were 60 to 80 percent smaller than their hips — regardless of their weight. They theorize that men unconsciously seek this body type because it signals that a woman is able to procreate.

5. He’s fascinated by your knowledge of medieval tapestries. Or whatever it is that gets you all hot and bothered—whether or not he shares the same interests. “It’s not about knowing facts—it’s about being passionate about something,” says romance columnist Mira Kirshenbaum, author of The Weekend Marriage. “These are things that are important to her, not just stuff meant to impress a guy.” This can be passion for a subject as seemingly obscure as agricultural practices of the Mayans or as popular as Spanish as a second language. He may not quite get it and he may not want to have all-night discussions about it, but he definitely appreciates the fact that you’re a smart, interesting woman who thinks for herself and doesn’t mold her interests to match those of her man. Your interests also fuel what Kerner calls the process of self-expansion. “The more you expand as a person,” he explains, “the more the relationship expands.”

6. He loves a good head rub from you. Don’t get me wrong—men love it when you grope their erogenous zones. But that’s not the only type of touch they crave. Adam, 28, of Roanoke, VA, confesses: “I love how my wife rubs my head at night.” Sweet, yes, but it also feels oh-so-good: Home to hundreds of nerve endings, the scalp is an often-neglected zone. And light touches anywhere can achieve a similar effect, since they cause his body to produce vasopressin, a feel-good relaxation hormone that also promotes bonding. Another positive side effect? Initiating any kind of physical contact sends your man the message that you want him just as much as he wants you—and that you truly care about him.

Matt Schneiderman has written for Stuff, Cargo, and Sync magazines.

59 Things a Man Should Never Do Past 30

1. Coin his own nickname.

2. Use a wallet that is fastened with Velcro.

3. Rank his friends in order of best, second best, and so on.

4. Hacky sack.

5. Name his "unit" his name plus junior.

6. Hang art with tape.

7. Hang The Scream, unless he stole it from the Munch museum in Oslo.

8. Ask a policeman, "You ever shoot anybody with that thing?"

9. Ask a woman, "Hey, you got a license for that ass?"

10. Skip.

11. Take a camera to a nude beach.

12. Let his father do his taxes.

13. Tap on the glass.

14. Shout out a response to "Are you ready to rock?"

15. Use the word collated on his resume.

16. Hold a weekly house meeting with roommates.

17. Name pets after Middle Earth characters.

18. Jokingly flash gang signs while posing for wedding photos.

19. Give shout-outs.

20. Use numbers in place of words or locations, such as "the 411" for information, or "the 313" for Detroit.

21. Hug amusement-park characters.

22. Wear Disney-themed neckties.

23. Wake up to a "morning zoo."

24. Compare the trajectory of his life with those of the characters in Billy Joel's "Scenes from an Italian Restaurant."

25. Request extra sprinkles.

26. Air drum.

27. Choose 69 as his jersey number.

28. Eat Oreo cookies in stages.

29. Volunteer to be a magician's assistant.

30. Sleep on a bare mattress.

31. End a conversation with "later skater."

32. Hold his lighter up at a concert.

33. Publicly greet friends by shouting, "What's up, you whore?"

34. Wear Converse All Stars with a tuxedo.

35. Propose via stadium Jumbotron.

36. Decide anything based on the ruminations of Howard Stern.

37. Call "shotgun" before getting in a car.

38. Dispute someone else's call of "shotgun."

39. Whine.

40. Mist up during Aerosmith's "Dream On."

41. Purchase fireworks.

42. Google the word vagina.

43. Ride a pony.

44. Sport an ironic mustache.

45. Hit 13 against a 6.

46. Organize a party bus.

47. Say "two points" every time he throws something in the trash.

48. Buy a novelty postcard in another country of topless women on a beach and write, "Wish you were here" on it.

49. Keg stands.

50. Purchase home-brewing paraphernalia.

51. The John Travolta point-to-the-ceiling-point-to-the-floor dance move; also that one from Pulp Fiction.

52. Put less than ten dollars' worth of gas in the tank.

53. Keep a minuscule amount of marijuana extremely well hidden.

54. Read The Fountainhead.

55. Watch the Pink Floyd laser light show at a planetarium.

56. Refer to his girlfriend's breasts as "the twins."

57. Own a vanity plate.

58. Whippits.

59. Say goodbye to anyone by tapping his chest and even so much as whispering, "Peace out."

Things A Man Should Never Do Past The Age of One

By Jasper Jacobs, age 17 months

Get circumcised.

Spend more than ten minutes looking at a checkerboard pattern (exception: peyote users).

Look longingly at his mother's breasts.

Urinate in his mouth.

Be terrified of Mr. Noodle on Elmo's World.

Cry at the sight of a wooden spoon.

Eat pureed Wheat Thins.

Suck on the corner of a laptop.

Go willingly into the arms of strangers.

Lose neck control.

Have a favorite Higglytown Hero.

"Make nice."

Wear a unitard.

Read The Fountainhead.

Find these and many more immature taboos in Esquire's Things a Man Should Never Do Past 30, available now. Buy it, use it, give it to a hopeless friend.