Dating

Describe the perfect first date

The company is obviously more important than the setting. That said, the setting would be a romantic restaurant, quiet so we can talk easily, with great food. There is instant mutual attraction between us, which we can both sense. We totally click/connect, talking for hours and hours about everything under the sun. We then go for drinks or a walk and can’t wait for our second date. The only problem is there is so much to talk about and not enough time.

Do you have a preference as to what a girl wears on a first date?

Not really, whatever makes her feel most comfortable.

Really? You really have no preference?

Well, since you asked, if you felt comfortable:

Sexy, form fitting dress
Pearls
Plunging neckline, lots of cleavage
Push up bra (no bra is fine too)
Short short hemline
Black lace stockings
High heels

But again, wear what makes you feel comfortable.

Any thoughts on dating and on-line dating in particular?

As the guy, I expect to do most of the pursuing, but I don’t want to do all of the pursuing. If I’m interested in you and you are in me, I will follow through and court you, but I also want you to take some of the initiative. Although you can’t really quantify it, I would say that in the ideal relationship, the guy is doing about 75 to 80 percent of the pursuing, with the girl doing the rest.

As for on-line dating, the signal to noise ratio is very low. You have to kiss a lot of frogs to find your prince or princess.

If in your initial encounters with someone, if they give any indication of being rude, a flake or a narrow minded dweeb, move on. The odds are overwhelming that you’re seeing the tip of the iceberg.

Avoid people who want extended e-mail communication before a phone call. Phone calls tell you more about whether you connect with someone than e-mails do. And the empirical evidence is clear that those who want extensive e-mails rarely step up to the plate. Most extensive e-mail communications never go any more. Presumably you’re doing on-line dating because you want to meet someone rather than find an e-mail buddy.

Get to a phone call as soon as possible. If on the phone you’re not psyched about someone, don’t meet; the odds that they’ll be better in person are low.

What about e-mails vs. phone calls?

People sometimes spend much too much time e-mailing back and forth. I much prefer to talk on the phone, because on the phone you can get a much better sense of whether you click with someone. If someone wants an extended series of e-mails before they talk on the phone, I’m the wrong guy. Some women place too much seriousness about the importance of a phone call. If you met someone at a party and he started talking with you, you’re not going to say, “I can’t talk with you because we haven’t exchanged two dozen e-mails first.”

I’ve discussed this with lots of friends who are doing on-line dating, and the clear consensus is: the more e-mails you have, the less likely you are to meet. The kind of person who insists on numerous e-mails before a phone call is usually someone who can’t step up to the plate and who does not know how to pursue a relationship.

I’m willing to do a few e-mails but that’s about my limit — I’m not looking for e-mail buddies. Some women say they can get a sense of someone through extended e-mails. If after reading this lengthy profile, you don’t have a fairly good sense of me, something’s wrong.

Don’t you want to get a sense of her?

Absolutely, but not through e-mails. I can get a much better sense of her through a phone call than via e-mails. Conversation is what causes me to fall in love, and I can get a pretty good sense of someone over the telephone. Almost all communication in a real romantic relationship is oral communication rather than written (people just don’t write long love letters any more) so why not go for the real thing rather than an artificial form of communication that doesn’t give you a good sense of whether you click.

But what if she wants to go slow and not rush into a phone call right away?

She’s probably not thinking very clearly. “Go slow”?? We’re talking about having a phone call, not getting married. A phone call is not some great stage of intimacy. At a party you do not “go slow” in talking with someone. If someone says “Hello,” presumably you start talking with them. And you can quickly end a phone call if you sense you aren’t compatible with someone. I even wrote an essay on this subject, Why E-mails are Useless in Judging Connection.

Any advice on dating, particularly suggestions on how to meet a high quality guy?

I thought you would never ask. Please see my essay.

Any advice on writing a personal ad?

I’ve read a few and it’s amazing how bad most of them are, so I wrote an essay on this subject.

Tell me about people being too specific.

The most common mistake people make in dating is they are specific in their checklist and they are too inflexible. An example of this is a very wealthy business executive who lives in New York. He has retained a dating service that specializes in searches. A friend of mine works there. Here is what he is looking for:

A woman who is between 32 and 37. (He is 52.)
At least 5′8″ tall
Blonde
Never been married
Protestant
Lives on the Upper East Side of New York
Comes from a socially prominent family
Has a graduate degree in finance or an MBA

The list goes on for another seven characteristics, but you get the idea.

This man is clueless about love. There’s nothing wrong with saying, “I’m attracted to tall women,” but to refuse to date a woman who is not tall is ridiculous. There’s nothing wrong with saying, “I find blondes to be appealing,” but to refuse to date a great woman who is a brunette is silly. His soul mate is likely a woman who is shorter, a redhead, a different religion, and doesn’t have a graduate degree in finance. If there is any justice in this world, this man will either be alone the rest of his life or will marry a girl who is primarily interested in his money.

Do you like it when a girl asks you out?

There is an unwritten rule that the guy asks the girl out, not vice versa. The girl can give all kinds of signs she is interested, but the guy is supposed to ask for the first date. (That also seems to be the case with the first kiss.)

That said, I LOVE it when a girl is interested enough in me to ask me out. It doesn’t happen that often but when it does, it’s very flattering. Whenever a girl initially expresses strong interest in me, I give her a second or third look, to see if I could be interested in her. I also love it when after a first date, a girl sends an e-mail right away saying she had a great time and would love to go out again.

So perhaps with most guys it would be a mistake for a girl to make the first move, but with me it would not be. Nevertheless, there is this unwritten rule in Boston, so I expect to make the first move almost all of the time.

What is your favorite sex/romance scene in a movie?

You’re probably expecting me to say something like

title=”9 1/2 Weeks”>”9 1/2 Weeks”
or the “I’ll have what she is having” scene from

title=”When Harry Met Sally”>When Harry Went Sally.” Nope. My favorite scenes are the verbal repartee with Katherine Hepburn and Jimmy Stewart and Cary Grant. That verbal ping pong (e.g.,

title=”The Philadelphia Story”>
“The Philadelphia Story” or
“His Girl Friday”), which goes back and forth so fast you can barely follow it, is the sexiest thing I’ve seen on film. The TV show “Moonlighting” (with Cybil Shephard and Bruce Willis) was also brilliantly written.

My second favorite scene was the sexual chemistry between Pierce Brosnan and Renee Russo in

title=”The Thomas Crown Affair”>
“The Thomas Crown Affair.”

Do you get a large number of responses through Internet dating?

Hundreds every week. In fact, in order to efficiently sort through all of them, I’m asking you to fill out a 25-page questionnaire. In addition, I’ve assigned you a code number: AF-413. If you could put that in the subject line of all e-mails you send to me, it will help me recognize you.

What do you think of on-line dating?

It totally totally sucks. The signal-to-noise ratio is way too small — too much noise, very little signal. I even wrote an essay on on-line dating.

So what would work well?

The most intelligent way to date would be to have a matchmaker, a yenta. She would meet in person every man and woman she introduced. See my essay on the ideal matchmaking service.

Do you enjoy dating?

I enjoy it and dislike at the same time. The best way to think of dating is as a necessary evil in order to have a long-term relationship.

You seem to have given dating a lot of thought?

I DO like to think and analyze things. As

target=”Socrates” title=”Socrates”>Socrates said, “the unexamined life is not worth living.” I’m fairly new to dating, having started again in Fall, 2001 after having been married for several years. I’m amazed at how brutal it can be, how rude some people can be, and how inefficient — and even absurd — the search process is. I am trying to understand it better, so when I meet people at parties, I tend to ask them a lot of questions about their experiences. That’s pretty much the way I am about everything — I ask a ton of questions, I analyze everything, and I like to come up with ideas and theories.