Good questions to ask

It’s important not only to be interested but to seem interested in your date by asking cool questions like the following:

_ What do you do?
_ What sports do you like?
_ What’s your favorite free-time activity?
_ What movies have you seen?
_ What restaurants do you like?
_ Do you think the president’s doing a good job?

Avoid questions like the following:

• Do you come here often? Trite, silly, and demeaning leading nowhere.
• How’s your food? The most common response is “Fine.” Complaining is tacky, and what are you going to do about it? If you want to focus on the food (I wouldn’t suggest it), you can offer to share. You can find out gobs about your date very quickly by his or her willingness — or unwillingness — to share.
• Can you believe the weather? Pleeeze try harder than this. It’s a deadend question that runs the risk of making you sound desperate. Good questions are those that draw your date out without putting him or her on the spot. The goal here is to learn about one another, not scare the daylights out of your date with your investigative prowess. You’re trying to show interest, not terrorize. Talk, explain, find out what makes your date tick a bit. It’s fun, so lighten up and follow these easy guidelines:
• Be prepared to talk about a lot of things. You can see why keeping up with current events, the latest movie, a local political scandal, or (in a pinch) your horoscope is a cool idea. If all you can talk about is work or your exes, it’s going to be hard to begin building those conversational bridges that give you the feeling that you’re getting to know someone and letting him or her get to know you.
• Don’t worry about your next question. Listen to your date’s response. It’s even okay to be quiet for a minute or two.
• Don’t fall into the Spanish Inquisition phenomenon.

Past sexual experiences

When in doubt, keep your mouth shut. If there was ever an area about which to draw a blank, it has to do with past sexual experiences. Over, done with, irrelevant. Don’t ask; don’t tell, even if tempted. You’ll both regret any departure from this policy.
All of us want to be loved not in spite of our warts but because of them. You want to feel that someone knows and loves the real you, but confessing sexual issues feels good for you for the moment but bad for the person who has to listen, and it will come back and haunt you both. See any pattern in the following list? You should. All these topics relate to past sexual experiences to keep a lid on:

_ Previous love affairs
_ Previous one-night stands
_ Previous indiscretions
_ Flings with the boss
_ Flings with your best friend’s significant other
_ Sexual preferences
_ Ménage à trois or more

If you have fantasies of being with someone else, remember that you’re not the only person who has occasionally thought about an old love or a movie star when you’re with your current date. The question is not “Is it okay?” but “How often does it occur, and how necessary does it feel?” If this type of fantasy happens most of the time, you’re not ready to be with this person. If it happens only occasionally and, in general, you’re pleased with your date, keep your mouth shut and enjoy the once-in-a-while forbidden pleasure of letting your mind wander.
You’re an adult, and human beings aren’t perfect. Learn from your mistakes and move on. Like everybody else, you’re a compendium of everything that’s come before: the people you’ve known (teachers, parents, sibs, the kindergarten bully, Sunday school teachers), the things you’ve done (your first kiss, dance lessons, strike-outs), and the things you’ve experienced (getting bad haircuts, developing crushes, receiving a favorite Valentine, getting a bloody nose, adoring favorite rock stars, losing report cards), and so on. Your sexual history is part of you, but the more you talk about it, the larger it’s likely to loom. And a looming sexual history does nothing but taint your current dating situation. If you need to confess about past sexual experiences, find a priest or a therapist, but with everyone else, adopt the Clinton plan: Don’t ask, don’t tell. You’ll both be happier and wiser.

When to say “I love you” (and when to keep quiet)

Few things are more memorable than the magical, angst-ridden, fingers-crossed, breath-held, passion-filled moment when either you or your date says, “I love you.” The phrase is much more than three little words. It’s also a silent question. As in, “Do you love me, too?” Properly managing this moment can spell the difference between euphoria and humiliation. Tips:

• Wait at least several months, a minimum of three but preferably longer, before confessing your true love — even if you feel it on the first night. It takes a while to gain and build trust. Zooming ahead too fast can easily backfire, and it’s really embarrassing to find out you changed your mind and you don’t really love ’em.
• If your date says, “I love you” and you don’t love your date back, don’t say “Love you, too” just to be nice. You’ll open a can of worms that’ll only make a gigantic mess.
• If you’ve been together a while and you’re just waiting for your date to spill the beans first, take a chance and tell him or her how you feel. Your date may be waiting for you to take the plunge.
• Realize that “love” doesn’t always mean the same thing to everyone. For some, the word “love” is followed by the word “marriage.” For others, “love” is always followed by “ya.” Make sure you’re clear on how you feel before putting your feelings into words, and give a thought to the way your date might receive what you’re about to say.
• Understand that true love implies commitment. If you’re not ready to be monogamous, connected, open, and loving, don’t say “I love you” just yet.
• If the only time you’re tempted to confess love is during sex or when you’re apart, close your mouth, open your eyes, and see what’s really going on.

How to Sharing Feelings

Setting guidelines on when to share feelings is a bit trickier. Admittedly, the coin of the realm for dating is feelings and intimacy, but in the early stages of dating, everything is a bit fragile. What you’re trying to do at this point is to set a firm foundation for everything to follow — but what this everything entails is almost impossible to predict.
A new dating situation is an investment between the two of you. You need to establish the ground rules together and get a feel for who both of you are and what you want all the while watching the interest mount, getting a return on your investment, and trusting the stability and reliability of the institution (that is, the idea that neither of you is going to rip the other off). Building this kind of trust takes a bit of time. Just as if you were to borrow money from a bank and be late on your first payment, the bank very well may see you as a bad credit risk and recall the loan. But if you’ve had the loan for years and have never been late or missed a payment, being late or missing a payment in year three will feel very different to both you and the bank.
When you share feelings, follow these basic rules:

• Be a tad cautious. Over exuberance (for example, taking a pledge of undying love) can feel pretty scary if it’s in the first 15 minutes of a date. No, you don’t have to be Gary Cooper, strong and silent, or Mata Hari, the keeper of mysterious secrets, but blurting out unformed and unexamined feelings à la Pee-wee Herman can scare the daylights out of both of you.
• Live with a feeling a bit before you express it. Make sure that what you’re saying is true for more than the moment. If you’ve just tripped over your date’s tennis shoe and you’re feeling angry, saying “I hate you, you slob” probably reflects emotions stronger than you’ll be feeling in ten minutes. If the sentiment isn’t going to be true for more than ten minutes, stifle it.
• Get some perspective on your own emotions and some control over your mouth before you speak. Otherwise, you can mislead yourself and your date. Saying “I love you” when you mean “Thank you” or “I’d like to have sex,” for example, isn’t fair or kosher, and it misleads both of you. As the two of you get to know each other better and feel safer and more comfortable with one another and develop some history, your words will have a context and can be evaluated that way. You’ll have a track record together and will have enough experience to know what is characteristic and what isn’t.
• In deciding what feelings to share and when, think about what would be reasonable to expect at any given time. A promise of undying love and devotion on the first date might feel kinda cool until you think it through. All of us long to be loved and appreciated, but on the first date? Nice — sorta — but completely unbelievable except in movies or romance novels or from folks who are a bit unbalanced, really needy, or really manipulative. So although “I really had a great time with you and I’d like to do it again. How about you?” isn’t quite as flamboyant as “Will you marry me? I knew from the first moment (five minutes ago) that you were the one,” it is a lot more believable. If you want to tell your grandchildren “We knew from the very first moment” 50 years from now, okay, but when in doubt, go slowly.

Guys’ proposing marriage on the first date is sorta cute and makes a girl feel really special. It also offsets the notion that all men are commitmentphobes who love ’em and leave ’em. But it is pure fantasy at best and blatant manipulation at worst. Dating should be fun, not a mind game or delusion.
So do share your feelings, but beware of temper and elation. Make sure they’re feelings you’ve been feeling for more than one second and can live with in an hour or two or a day or two. If you really must say it, finesse a bit — for example, “I know it’s too soon to be feeling this, but it sure feels good to me right now” — and then laugh sweetly. Trust is a fragile thing. You need to trust not only each other, but yourself.

Things to tell if asked or pushed

The preceding sections outline the type of information you should share at some point in the relationship. But what about the information that you’re not obligated to share but have been asked for? You know the type of questions: the ones — like “How many relationships have you been in?” — that come out when you least expect it and leave you sputtering in your dessert. Do you avoid answering? Subtly change the subject? Look at your date like it’s none of his or her business (which it isn’t, really)? Or just ’fess up? Although historical accuracy isn’t required in answering a question like this — in other words, you can avoid giving too much detail (think of Andie MacDowell’s character in Four Weddings and a Funeral) — if you stonewall completely, you’re likely to make your date think you have something to hide. So the best answer is to give a brief history — more or less what you’d put on an entry in who’s who in American dating circles — and then move on without editorial comment that includes who, how long, how many, or preferred positions. Some questions are so hard to answer that you really should feel compelled to answer only if you’re pushed — that is, if your date won’t let the subject drop and not answering is likely to hurt the relationship more than a tactful but honest answer would. Some questions that fall into this category are

• Why didn’t you have an orgasm?
• What is wrong with me?
• Why don’t you like my friend?

Things to tell eventually

Sooner or later, the I’ll-do-anything-you-like-to-do phase has to stop; not only is it boring, but it’s also not entirely honest. After all, you must have some likes and dislikes. They’re what make you the person you are, and jettisoning them all in the interest of harmony is a short-sighted perspective. At this point (I’m talking date three or four, max), you want to be honest about who you are and what you enjoy doing. This information is not first tier — it doesn’t need to be understood as the bedrock facts of the relationship on date one — but it is important enough to be risked even if the result is mild turbulence; otherwise, you run the risk of being trapped by your pretenses. If you can’t keep up the ruse forever (and you can’t), it’s best not to keep it up at all. But realistically, at the beginning of a dating experience, we all resonate a bit; we want to be liked and likable and agreeable, and so we soften our own preferences because we want the relationship to endure. But sooner or later, the real you has to come out, and the sooner the better. After all, you want as few unpleasant surprises as possible.
Almost everyone has strong feelings about something. See if I push any of your love or loathe buttons with the following:

• Aerobics
• Football
• Ballet
• Bullfighting
• Boxing
• Sky diving
• Types of food (Chinese, Mexican, French, and so on)
• White-water rafting
• Your date’s

• Perfume or aftershave
• Temper
• Drinking
• Sense of humor
• Socks
Note: As you get seemingly closer to the loath side of the list, it becomes even more important to temper your firm opinions with gentleness.
As you share your likes and dislikes in the name of honesty, be gentle. Telling
someone you’re not crazy about football may be jarring to a die-hard fan, but
you need to be especially careful about mouthing off about your date’s

• Best friend
• Parents
• Dog
• Hair color
• Haircut
• Height
• Weight
• Religion

Things to tell immediately

If there’s something about you that you think can affect any long-term prospects and that more than two people know, you may as well ’fess up on the first few dates — especially if you feel that it may blow things. You can try to create an environment that makes sense, but keeping that big of a secret from the get-go adds pressure and nervousness at a pressurized time. If you’d tell a same-sex potential friend, tell your date. If your date is cool about it, you’re relaxed. If not, at least you haven’t invested much already. Information that more than two people have isn’t a secret. If your date is likely to find out sooner to later, you may as well tell sooner rather than jeopardize the relationship once it progresses and the additional factor of trust is introduced (as in, “If you’d lie about this, what else haven’t you told me?”). Any long-term relationship is based on trust. If you can’t trust someone, you can’t love that someone, so don’t start off hiding important facts. The list of things you definitely must share includes most of the biggies in life. You should share this information by the third or fourth date. Any earlier is unnecessarily brutal; after all, if you really don’t fancy one another, why parade the skeletons from your closet? Any later is viewed as a breach of trust (plus, not having shared can get you in more trouble than any upset that telling may now create).

• Previous marriages: How many times you’ve been married, how long you were married, and how long you’ve been apart. But don’t go into too much detail. See the later section “Keeping Mum.” Notice that you should confess previous marriages, not whether you’re married or separated or in the process of divorce. The reason? If you are married or separated or in the process of a divorce, you have no business dating at all — not until one full year after the divorce is final. I’m not kidding here. If you fit into one of these three categories, you can hang out with friends, work out, paint your house, become a temporary workaholic, take courses, volunteer — but you can’t date.
  
• Previous convictions and parole violations: What crime you were convicted of and how long you were in prison. (I’m sorta kidding here, but stuff happens.)
• Previous bankruptcies: How long ago you filed for bankruptcy and why.
  
• Previous kids: How many, how old, whether they live with you, and if they don’t, how often you see them.
• Previous sex change operations: What can I say? When should you share this information? You don’t necessarily have to share it when you first lay eyes on one another, but before the end of the third date at latest. Confessions of any kind — even “I think you’re swell” — need to be seen and heard in context. The best rule for when to tell is when you’d want to know if you were the one about to hear what you have to say.