What I Seek in a Companion

Desirable Traits for a Companion

The two most important characteristics are manners and kindness to friends and strangers. By manners, I do not mean Emily Post, but basic kindness and courtesy to others, particularly strangers. (Most people are nice to their friends.) I look at how people treat waitresses, for example. I’ve learned that when things are not going well, you will be considered a stranger, and if she has no trouble treating strangers badly, she’ll treat you badly.

(Several women I’ve met — both in person and online — have been rude, and this has surprised me. I do not lead people on and I don’t play games. If I’m interested in someone, I let her know, as soon as I know. If I’m not interested in someone, I will also let her know, in the kindest and least hurtful way I can think of. I respond to all e-mail I receive. I’m always courteous to people but in dating, particularly online dating, I bend over backwards to be nice to people.)

I like women who are present, who focus completely on whomever they are talking with. With most people you meet at parties, they’re on some other planet, a planet that hasn’t been charted, let alone named. Bill Clinton has this ability to focus on who he is talking with. I’ve never met him, but people who have say that when you are with him, you feel as if you are the most important person in the world. I like people who are totally there.

Intelligence is very important to me, as is intellectual curiosity and a wide range of intellectual interests. I want someone I can talk with (both emotionally and intellectually) about anything and everything, who challenges me and makes me think. She is constantly learning new things.

Very, very verbal and highly articulate. Conversation is what causes me to fall in love.

High bandwidth, someone who can handle my intensity

Outgoing. The famous Boston reserve never did much for me.

Social grace, social charm and poise, those who make others feel comfortable, and who are inclusive. Imagine four people at a party talking to each other, with a fifth person standing nearby, alone. Someone who is inclusive would invite the fifth person to join the conversation. I like that. Most people in Boston simply ignore the fifth person.

You should enjoy going to parties, like to socialize, and enjoy meeting interesting people. I have made numerous interesting friends and after several dates, I would want introduce you to them. She enjoys dressing up and attending black tie events.

Someone who is passionate about life and love

Empathy and emotional intelligence

High energy is so, so, so attractive.

Optimistic, who has positive energy who views the glass as half full, rather than half empty. As Americans living the most interesting time in history, we have so much to be grateful for.

Femininity, someone who is a girly girl. Someone who is very comfortable with her femininity and likes being a girl. Acting girlish now and then is a big plus. (Southern women are taught from an early age how they can have a guy wrapped around their finger. The men prefer this because they are totally enchanted, and the women obviously like this because they have the power — a real win-win.)

She is highly romantic and incredibly affectionate, who is comfortable with tasteful displays of public affection (“PDA”) and loves to cuddle for hours. And I do mean for hours.

Emotional stability and maturity are important, as is inner strength.

Loyalty is key.

A great sense of humor is essential.

I prefer someone who is fairly normal — If you’ve died your hair purple, if you’ve pierced your tongue, or if you worship

Satan, I’m the wrong guy for you. In addition, call me old fashioned, but I prefer women who have not undergone sex change operations, so it’s essential that you were born female. At the same time, I prefer women who are unconventional in some way.

Someone who is serious about self-improvement, who is not completely satisfied with how they are, and is looking to improve in some way. We all have our faults and it’s important to try to improve oneself over time.

I like directness, those who say what they are thinking rather than my having to guess what they are thinking. It’s so much easier that way. I insist on courage — if things aren’t working out, say so, rather than not returning phone calls. People that avoid difficult issues are simply cowards.

I’m not into playing games or many of the silly rules that have developed in dating — e.g., you can’t call someone the next day after a first date, because that makes you look too eager.

I prefer women who dress well. Most guys love it when a girl dresses up for a first
date — it’s a sign she is psyched. I love the little black dress. (An excellent article is

“In praise of the little black dress: This classic item is always in style” by Anna Johnson.)

Someone who is serious about wanting an emotionally intimate and loving relationship and is willing to invest the time and energy to see how far a relationship can go. Someone who is over their ex and whose baggage is not excessive (can fit into the overhead compartment).

I want someone who can step up to the plate if she is interested in a guy. I like it when on the first date both of you have a strong interest in the other and you both want a second date right away.

Finally, I’m looking for someone who is intelligent in how they approach romantic relationships, who doesn’t have a lot of stupid rules. (You’re one year older than my age range, or I play golf and you don’t, so I won’t date you). High quality guys are rare, particularly in Boston, and an intelligent girl who is seeking a high quality guy recognizes that and tries not to have too many arbitrary rules. (As for me, I do realize that high quality girls are rare, and if someone is high quality, I look for reasons to date her, not to exclude her.)

Some of these are deal breakers and some are mere preferences. I hope I’ve been clear which is which.

Did I mention high energy?

Anything else?

A few minor things:

First, I prefer people who understand the concept of a mobile phone. If you’ve got one and you’re meeting someone for a date, the idea is to keep it on so that he can call you in case he is unable to find you or is running late. I know the concept is not a difficult one, but an amazing number of women don’t seem to understand it.

Second, I like people you can actually get hold of. With some people, the only number they have is a mobile phone, which they never answer, and it takes two days for them to get back to you. I prefer people who are accessible, who can be reached, and who return telephone calls quickly. Warren Buffett — presumably a busier person than I or anyone I might date — returns all calls within an hour, if at all possible.

Third, I have a preference for people who know how leave voice mails. Recently a guy named Robert called me. He left a 15 minute message and at the end left his phone number, saying it much too quickly to write it down. So I have to play the entire message again, listening to his 15 minute message, and then I try to decipher his phone number. Why not say, “This is Robert calling. My number is xxx-xxxx” and then leave the 15 minute message? That way, if I have to play the message again to listen to his number, I can hear it at the beginning, rather than having to listen to the 15 minute message again. (And by the way, why is Robert leaving me a 15 minute message in the first place, rather than waiting for me to call back or sending an e-mail?)

How important is intelligence to you?

Very, very important. Most guys want a girl who’s about 10 IQ points less than him. More than 15 IQ points less, she’s too dumb — few men want to become seriously involved with a bimbo. Less than 10, she starts to threaten the tender male ego (the most fragile thing there is). I’m different — I have no problem if she is smarter than I. (And I’m talking about intelligence conventionally defined — abstract reasoning, logical thinking, the ability to make comparisons, generalizations and deductions. I’m not talking about “I can’t add 2 plus 2, but I can make pencils, so I’m intelligent.” There is some flexibility in this, such as those who are artistically gifted or who have extraordinary social and emotional intelligence.)

I’ve never understood it when people are unwilling to date someone because he or she is superior to them in some way. I’ve heard women say they didn’t date a guy because he was so much smarter than they were, or he was more outgoing, or too high energy, or whatever. As for me, I have no problem if she is superior to me in every way. If she is smarter than me, is more outgoing, is better looking, is more successful and accomplished, speaks more foreign languages, has visited more countries, is a better athlete, if she outclasses me in every way imaginable, and she wants to go out with me, why not?

What do you mean by intelligence and intellectual curiosity?

It’s a combination of five factors:

General intellectual ability — i.e., the ability to think abstractly and to make generalizations, to think and reason logically — what psychologists call “g” (for general intelligence)
What kind of training have they had in developing their intelligence? (I’ve been fortunate in that since prep school, I’ve always had close relationships with mentors who taught me how to think.)
Intellectual depth — Can they think deeply about a subject?
In which fields are they knowledgeable? (I like women who know a lot about many different things.)
Are they intellectually curious? Knowledge has expanded so much that no one can be a Renaissance man or woman any more. I like women that are at least interested in the fields they are not particularly knowledgeable about. One girl that particularly impressed I met a black tie social event. She attended the London School of Economics, so I asked her, “What else are you interested in, in addition to politics and economics?” “Everything,” she responded. Good answer; I knew right then I wanted to go out with her.

How important is it that she be a good conversationalist?

Miss Right need not be a good conversationalist, she must be a great conversationalist. By that I mean:

She has interesting and insightful things to say. She knows a lot about a lot of different things.
She likes to talk about important stuff, rather than the weather and how the Red Sox are doing.
She is highly articulate and verbal. She is able to articulate her thoughts and her feelings. She is emotionally communicative.
She is very direct. If she thinks I’m acting like a jerk, she says so, but gracefully.
When an interesting idea or issue comes up, she takes the detour and explores it, but eventually gets back to what we were talking about.
She has an insatiable intellectual curiosity and needs to be constantly learning new things. Her attraction to me is based to a significant extent on what she can learn from me.
She is good at asking questions and drawing me out.
She is good at handling me in a conversation, as I tend to ask zillions of questions. She’s able to answer questions well and then parry back with her own questions, moving the conversation forward.
She loves to talk and she loves to listen. She gives good phone.

Conversation is what causes me to fall in love. The girl I’m going to fall in love with is someone I can talk to for 5 hours and want to continue. When you talk, it’s frustrating because there are always five things you want to say to the other person, and you have to keep choosing what not to say.

The best relationships are those where she and I talk roughly the same amount of time — e.g., over ten dates, one of us talks no more than 60 percent of the time and the other talks no less than 40 percent of the time. I like highly interactive conversations, where there is constant questioning and probing, with comments being added by the other all the time. She needs to be verbally facile and to be able to think on her feet.

What are the three levels of conversation?

On a first (or subsequent) date, your conservation could be at one of three levels:

You’re both looking for things to talk about, and there are lots of awkward pauses in the conversation, with the two of you just looking at each other, trying to figure out what to say. Not much fun.
Conversation flows smoothly, with little or no awkward pauses.
During much of the time, there are so many things you want to say to the other person, that you have to repeatedly restrain yourself. You have to repeatedly choose one path of conversation, trying to remember for later the three other paths that come to mind, because you also want to discuss those.

Level III is absolute heaven.

What do you mean by social poise?

Social poise means putting the other person at ease. A woman I met named Tricia would win the Nobel Prize in social poise if one was given. I was at the bar in the Bristol Lounge in the Four Seasons (this was before I realized that bars are a waste of time in order to meet people). I noticed this tall, attractive women talking to a friend. I introduced myself. She turns around, has a great smile on her face and says, “Hi James. I’m Tricia. This is my friend Sharon. Why don’t you sit next to me; I’ll move my stuff from this chair. James, I live in Boston and Sharon lives in Brookline. Where do you live?” In two seconds she put me completely at easy and we talked for 4 hours. That’s why I mean by social poise. Obviously Tricia is in a league by herself and I don’t expect everyone I date to come close to her. But I would like some level of social poise.

Are there any particular kinds of women you’re attracted to?

I’ve always been attracted to women with a strong interest in the arts and humanities — classics, literature, writing, music, drama, dance and the fine arts. Extra points if she is actually creating or performing art, rather than analyzing it.

Entrepreneurs are always interesting — if they’re successful, they have to be talented in so many different areas.

Women who have traveled extensively, have lived in other countries, and/or speak several foreign languages are always of interest.

None of the above are essential, it’s just some of the types of women I find appealing. What’s most important is whether we connect.

What are you not looking for?

Smoking

Flakiness. I like people that show up on time and that return telephone calls and e-mails promptly.

People that are self-absorbed, who are totally into themselves. At some of the artist parties I’ve gone to in the South End, a significant number of the people were totally self-absorbed.

Those who are narrow minded and who have dumb, stupid rules — ”I’m an academic and I only want to date an academic.”

I lose interest if a girl plays hard to get. It’s just another form of game playing and I have zero interest in games. Life is too short. A girl should be mature enough and have enough experience with relationships to know what she wants, and if she wants me, the way to “land” me is to express interest, not play hard to get.

Those who don’t know what they are looking for in a partner

Those who date when they are not ready because they are not over their ex