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.

Volunteering Information

What information you share — and when — depends on who you are and your level of comfort with openness and who your date is. If your date is open and friendly and accepting, you most likely feel comfortable sharing more. If you’re dating someone reserved, you’re likely a bit less forthcoming. This is called mirroring and survival and common sense. Some people are quite comfortable sharing some parts of their lives and less comfortable sharing other parts. What you’re trying to accomplish early on is compatibility — a good fit. So volunteer what you’re comfortable having most people know about you. The rest you can slowly divulge as the relationship progresses; in other words, you don’t have to produce an autobiography, complete with a slew of your opinions — or your most awful secret or family scandal — all in the first couple of dates. Most people who date have a mini-scenario worked out in their heads of what they want someone to know about them. You, too, can create a mini-script —what you’d tell someone on a long airplane trip, for example, or someone at a party is a place to start:

• Include a little bit about your factual life: You know — things likewhere you’re from, where you went to school, how many brothers and sisters you have, what hobbies you like, what kind of work you do, and how you spend your free time. In other words, this script can more or less include the stuff you’d put in a personal ad if you had unlimited space and money. (In a way, the early days of dating are a personal ad — you share who you are and what you want — with the advantage being that your date gets to respond immediately, without writing to a post office box.) Age and weight are optional.
• Share feelings: Worries, music groups that you like, whether you’re a baseball, opera, or chocolate fan, and how the weather is affecting you.
• Keep the script positive and realistic: Your comments shouldn’t be too negative or make you sound like the best thing since sliced bread. Selfeffacement works only for Woody Allen, and a braggart isn’t much fun to be around.

When you share information, keep the following in mind:

• As the two of you get to know each other, remember that you really don’t know each other. If the date doesn’t turn out well, this person is going to have all the information you’re now blabbing.
• Make sure that you’re not using information as a way to bind someone to you too soon and too tightly. This tactic usually doesn’t work anyway, and you’ll hate yourself in the morning for telling someone you don’t plan to see again that your family’s completely dysfunctional and you’ve been in therapy since third grade.
• Exchanging information is like dancing — you have to move together, or it doesn’t work very well at all. Some people are comfortable volunteering

some things; others are comfortable volunteering other information. Just because you describe the house you grew up in doesn’t mean that your date has to blueprint his family homestead. The key is to make sure that you’re not doing all the talking or all the listening. Once the two of you really get to know each other and have moved from first date to first month to first year, the ratio of what you don’t talk about to what you do does — and should — shift dramatically. After all, you don’t want to not tell anything that, after being found out, will shake the pillars of your relationship. But too much too soon is without a context for understanding.

The Last Fifteen Minutes of a Second Date

Two words: No sex.
Two more words: Too soon.
Even though you feel like you’ve known each other all your lives, it’s really only been two nights, or an afternoon and an evening, or ten minutes and lunch. You get the picture. You don’t know each other — don’t get to know each other under the sheets.
Physical intimacy blurs the emotional intimacy of a relationship. It’s hard to see things clearly when hormones are involved. A second date isn’t even a relationship yet, so sex confuses the whole deal. Making out is okay. Making out passionately is cool. Just don’t go any further than that until you know each other better. Ask yourself if you’d be embarrassed the next day if the previous night of lovemaking turned out to be a disaster. If the answer is “well, yeah,” then the answer to sex has to be “well, no.” Never have sex with anyone whose middle name you don’t know.

Trust or Consequences

Trusting someone instantaneously can be just as devastating as suspecting an ulterior motive behind everything he or she says. True trust takes time. No shortcuts allowed. Remember: Your date is just your date; he or she isn’t your friend. Even if you’ve been chatting for months online, trust still takes a lot of together time. If your date wants you to give more than you’re willing to give at this early stage, don’t be afraid to say so . . . and stick to your guns. If, on the other hand, you don’t want to “slip” and divulge any clues as to where you live or work, what you do for a living, or what color your hair really is, you may be a touch paranoid. Yeah, the world can be a dangerous place. But if you trust someone enough to agree to a second date, it’s only fair to let him or her get to know you. This isn’t a CIA investigation. It’s a date. Chill out. Particularly if you’re over 30, avoid what I call the Blitz School of Dating. That’s when you’ve been there, done that, and you don’t want to waste any time. You want to book a table in a quiet restaurant where the waiter won’t bother you for the two hours you take to chronologically pour out your life story, hear your date’s, and determine if this union has legs. While the Blitz approach has been known to work on occasion, I don’t recommend it. Part of the mystery and magic of getting to know someone is getting to know someone, not hearing how well they know themselves Finally, resist the temptation to ask yourself the $64,000 question: Is this the one? Is this second date with the person with whom you’ll spend the rest of your life? Have babies with? Rock on the porch with? Watch go gray? While the urge may be there to weigh every second date on the “forever scale,” don’t give in to it. Distract yourself. It’s too soon. A relationship hasn’t even taken flight yet.
If your worst enemy knew what you’re telling your second date, could he or she use it against you? If the answer is yes, keep it under wraps for now. If not, go for it.

Getting to Know You

The info-exchange process on a second date is fun and exciting and interesting and a bit tricky. Unlike a first date, which is pretty superficial, a second date delves a little deeper. You already know you like each other enough to find out more. How much more remains to be seen. For now, you want to be vulnerable enough to let your date see who you really are without showing all your warts at once. (A wart or two is okay.) You want your date to feel comfy enough to share a wart or two with you.
To get the good stuff, you’ve got to give it. Trust me — your date won’t open up if you just sit there with your arms crossed. Though a second date usually shifts the conversational focus away from you and onto your date, striking a balance between being a good listener and an interesting and sincere talker is crucial — and not always easy or comfortable right away. First, know your personality type before the second date even starts. Are you the strong, silent type? A Chatty Cathy? Knowing who you are can help you tone down your natural tendency to clam up or blab on and on.
Second, periodically gauge how things are going. Here are some basic rules:

• If you feel you know everything about your date and your date knows nothing about you, it’s time to open up.
• If your date has been nodding for the past hour, it’s time to hush up.
• If your time together seems more like a stand-up routine than a conversation, take a deep breath and focus on getting more insight, less laughs.
• If your date sounds more like a job interview than a chat, it’s time to get a bit more personal.
• If your date blushes each time you ask him or her a question, it’s time to get less personal.
• If the conversation on your second date keeps grinding to a screeching halt, ask yourself if it’s you or your date. One of you is uncomfortable. It’s okay to flat-out say, “We had such fun the last time we went out. Is something making you uncomfortable?” If the answer is no and the conversation still limps along, you may be looking at a second, and final, date.