The Competition: The Adventurer

The next type of man that just might be your competition is the Adventurer.

Definition: The Adventurer went to a really good university but didn’t graduate. Instead he started a business that made him rich by the time he was thirty. He likes to try new things but isn’t rash like the Bad Boy (I‘ll discuss him on Tuesday). He doesn’t typically live in one city for more than a few years.

What He Has that You Don’t: Risk-taking gene. An interesting life.

The Type of Women He Attracts: Other Adventurers. Thrill seekers.

What It Tells You about a Woman if Her Last Boyfriend Was an Adventurer: She’s spontaneous. She spends her weekends and evenings out. She’s physically active. She’s moving to Shanghai next week.

What to Do to Be More Like Him:

Physical attributes: Tan. Work out by rock-climbing or training for (and doing) an Ironman.

Hobbies: Sail. Race. Travel. Start businesses. Sell said businesses.

Behaviors: Say ‘yes’ to most requests to do something new (spelunking, going on a photo shoot of polar bears in the Arctic, filling in for Warren Buffett doing a talk at the last minute).

What to Do to Win Over a Woman When He Is Your Main Competition:

You’re in luck if he’s just been transferred to another country by his company. Unless she’s willing to follow. In which case you’re screwed. Better luck next time. Of course, if she isn’t following him, it’s probably because she already had plans to move to New York. Don’t you bother following her. You haven’t a chance with her unless you’re an Adventurer yourself. And if you are, you don’t need me to tell you what to do to win her over. If an Adventurer is your competition, move on. He has you beat.

Up next: The Bad Boy

The Competition: The Charmer

With the Charmer, I move into talking about rivals whom you might actually want to be like.

The Charmer.

Definition: He’s suave. He’s good looking. He orders his martinis shaken, not stirred.

What He Has that You Don’t: Social skills. Good looks. Fashionable wardrobe. Great body. A cool car.

The Type of Women He Attracts: 20somethings.

What It Tells You about a Woman if Her Last Boyfriend Was a Charmer: She’s too young for you.

What to Do to Be More Like Him:

Physical attributes: Dress better. Work out. Perfect your smile (braces, whitening).

Hobbies: Dance (club dancing and swing dancing). Play guitar. Sing. Write songs/poetry (no prerequisite for them being good.

Behavior: Talk primarily with women. Flirt/smile all the time. Have lots of female friends.

What to Do to Win Over a Woman When the Charmer Is Your Main Competition:

You’re likely screwed if she’s already enamored with a Charmer. Even if he spurns her, she will still be infatuated with him for a year or so and not be interested in going out with anyone else. And, no, trying to be her shoulder to cry on will in no way work.

If she hasn’t totally fallen for him, though, you can edge out the charmer by being more available. Charmers typically have a number of possibles in their lives. Show her she has no competition with you. This can be a dangerous move--it could make you seem unattractive--but it is a necessary move. If you want to be devious, set things up so that she sees *her* competition flirting with *your* competition, the Charmer. The more unavailable he seems, the more interested she will be in you--provided you are a Sensitive Guy. Sensitive Guys are the less socially adept, but more spiritually deep, version of the Charmer. I’ll write about the Sensitive Guy next Tuesday.

Up on Friday, the Adventurer.

The Competition: The A**hole/Loser/Addict/Abuser

The third type of man that could be your potential competition in the world of dating is the Loser.

The A**hole/Loser/Addict/Abuser.

Definition: He’s utterly egotistical. The feelings, wants and needs of others are of no consequence to him. He’s a user: of people and/or controlled substances.

What He Has that You Don’t: Ability to accept himself as he is.

The Type of Women He Attracts: Women with low self-esteem. Women who are rescuers/martyrs.

What It Tells You about a Woman if Her Last Boyfriend Was an A**hole/Loser/Addict/Abuser: She needs to be rescued--from low self-esteem and/or from a crappy life situation.

What to Do to Be More Like Him:

Physical attributes: Lose weight. Dress casually, always in jeans and t-shirts.

Hobbies: Use drugs. Drink.

Behavior: Make fun of people. Hit things. Break things.

What to Do to Win Over a Woman When the Asshole/Loser/Addict/Abuser Is Your Main Competition:

You want to seem like you need rescuing while still being cool. You might get her to sleep with you once if you come off as pathetic (“I’m still a virgin at thirty”), but you’re not going to get more sex than that or more relationship than that. There has to be something in you that she sees as hip. It’s difficult to pull off if you aren’t a heroin-addicted bass player. So unless she’s in a place where she recognizes *her* need to be rescued, you’re probably out of luck. If she *is* in a place where she wants to be rescued, just being nice to her will actually work. If it doesn’t work, she hasn’t hit bottom yet. You can wait in the wings for that to happen and swoop in with a dinner invite. You pay. Bring flowers but not roses. They’re overkill on a first date. Try a single Gerbera daisy.

On Tuesday, The Charmer.

The Competition: The Man

The Man.

Definition: He’s into money, power, expensive toys (electronics, cars, etc.). He’s basically a soul-less Frat Boy all grown up.

What He Has that You Don’t: Money. Power. A manly face and body. Hugo Boss and Armani suits.

The Type of Women He Attracts: Shallow women. Women who want to be taken care of. Princesses.

What It Tells You about a Woman if Her Last Boyfriend Was The Man: She expects too much. You better have a house, a substantial stock portfolio and be willing to foot the tab every time.

What to Do to Be More Like Him:

Physical attributes: Bulk up. Look older: dress more formally, shave or grow a beard (which makes you appear more mature), and/or get glasses.

Hobbies: Invest. Drink scotch (and know the difference between single malt and double malt).

Behavior: Engage in all types of chivalry, including paying the check, opening doors for her and standing up when she leaves the table. Talk about money (how much you make, how to earn more, where to invest it, what you’ve recently spent it on).

What to Do to Win Over a Woman When The Man Is Your Main Competition:

If you can’t compete financially, walk away right now. If you can afford to date the kind of women that are attracted to The Man, you can get an edge on The Man by being more explicit about your financial situation than he’s likely to be up front. Let her know you’re willing to support a life partner financially. Play up anything in your life that speaks to your stability, like having been with your company for ten years, any recent promotion or owning a home. Geeks often have money but are reluctant to make it known, either verbally or by their actions. You can count on The Man to drive an expensive car and have a good haircut. The Man may have a bit of tact initially and refrain from talking about his possessions, but it will be obvious that he does have money by the new Audi he drives. Don’t let the woman forget that the geeks are the ones making the money these days and that you’re as (or more) financially secure than The Man.

On Friday, The Asshole/Loser/Addict/Abuser

The Competition

Today I start discussing your competition: how to be like them, and how to win against them.

I’ll be writing about various “types” of men. Each entry will define a type, what he has that you don't, the kind of women he attracts, how to be more like him (including physical attributes, hobbies and behavior), and, the key ingredient, how to win over a woman when that type is your main competition.

It goes without saying (but I’m saying it anyway so you don’t think I’m a complete idiot when it comes to the complexities of human psychology) that real people are, of course, more complex than a stereotype. But stereotypes do have some truth in them, and labels have some social functionality.

So apply and use as you see fit.

I’ll begin with the types probably don’t want to be. Up today: The Frat Boy.

The Frat Boy.

Definition: A universal type who needs no definition.

What He Has that You Don’t: Athletic build. Privileged background. Trust fund.

The Type of Women He Attracts: Desperate women with no self-esteem.
What It Tells You about a Woman if Her Last Boyfriend Was a Frat Boy: She might put out and not care how bad you are in bed.

What to Do to Be More Like Him:

Physical attributes: Work out. Wear baseball caps and sports jerseys.

Hobbies: Drink. Watch sports. Play sports. Play practical jokes.

Behavior: Get drunk. Engage in homophobic jokes.

What to Do to Win Over a Woman When a Frat Boy Is Your Main Competition:

Pay attention to the woman; actually listen to her because he won’t. Take her sexual innuendos in stride, don’t show embarrassment, and don’t ignore the comments. Rather reply with sexual innuendo. Make her laugh--usually with sexual innuendo or by making fun of the Frat Boy. Just don’t be too cruel or she’ll defend him. Or he’ll beat you up.

On Tuesday, “The Man.”

What to Say (Conversational Skills, Part 7)

In order to be an adept conversationist, you will also need to know how to change the topic of conversation.

The last conversational skill I’m going to write about is how to change the topic, either because the old topic is now dead/boring or because you want to talk about something else for whatever reason. Please note that you should not try to change the topic of conversation if the woman still seems into the old topic. It’s rude and dismissive.

Also note that if you attempt to change the conversation topic by telling a story right after someone else has told an anecdote, make sure that your story relates in some way to the previous one. For example, if she tells about a horrible car accident she was in while driving through Nevada, do *not* follow up with a story about the time you were in Nevada that has nothing to do with a car accient. Her story was about a car accident, not Nevada. Some people seem to be under the misguided assumption that they are cleverly changing the topic by picking up on some tiny irrelevant detail and running with it. Occasionally this works. Most of the time, however, it comes off as a desperate need to be the center of attention. It seems as if you have been breathlessly waiting for something, anything, to come up in her story that you could use to bring the conversation back around to you. And when you change the topic so suddenly from car accidents to Nevada, it seems dismissive of the prior conversation, as if car accidents (and she) so bored you that you had to change the topic to Nevada.

So how do you change the topic of conversation?

Instead of addressing the particular details of a story or a conversation topic, respond with an emotional reaction. Maybe car accidents really do bore you (or make you anxious). You can move the conversation away from car accidents by making a statement about your emotional reaction to something related to car accidents, such as “I would have been so freaked out after that, I don’t know that I would have wanted to drive again.” And then the conversation can flow away from accidents to how people get over traumas. Or maybe it’s not that you’re bored with a conversation but you don’t know anything about the topic of conversation, so you’re stymied for words. Again, bring in an emotional reaction. You may not know details of art history and what movement Matisse was part of and what that meant to the culture at large, but you know what a Matisse looks like and you have an emotional reaction to it--of curiosity, perhaps, or dislike.

Another way of changing the conversation topic is to ask a question and move to a generality. There are questions that will further the conversation on the same topic, and there are questions that will begin to divert it away. Let’s say the conversation is about William Faulkner. You could ask about his influences, or ask her to explain The Sound and the Fury to you. But this would not lead you away from the topic. Instead ask a question that may be wrong (whether it is or not does not matter)--such as “Did Faulkner commit suicide?” She’ll say, “I think you’re thinking of Hemingway,” or “No, he was just a raging alcoholic.” Now you can continue to move the conversation away from Faulkner specifically and talk more broadly about, for example, why artists are so self-destructive. Naturally, you might not want to discuss that, but you get the idea. Use a question to move the conversation to a broader topic you do want to discuss.

A third way to change the topic of conversations is to ask a question and move to a specific topic. Maybe the conversation is a general one about why artists kill themselves, and you just read “The Old Man and the Sea” and you want to talk about that book. Happily for you Hemingway committed suicide, so you’ve got an easy path into talking about his novel.

Now that I’ve discussed coming up with good answers to dull/annoying/embarrassing questions, how to tell an anecdote, and how to change the conversation topic, on Friday I’ll move into discussing how you can compete with specific types of men for the attention of the woman you’re interested in.

What to Say (Conversational Skills, Part 6)

Last time I wrote about the questions you need to be prepared to answer in a social situation, Today, I’m writing about how to tell an anecdote.

Think of the people you know who tell really good stories at parties. What about the way s/he tells the story makes it interesting? Make a study of those people and learn from them. In the meantime, here are a couple of tips:

Exaggerate. But don’t indulge in hyperbole. The story will come off as if a ten year old were telling it if you use hyperbole. Make the exaggeration realistic, like it could have happened that way even if it didn’t.

Feel, Don’t Think, Before You Talk. I know you’ve probably been told all your life to think before you speak. After all, you don’t want to sound foolish, or, God forbid, be wrong. This censoring of yourself is why you think you have nothing to say or that you aren’t clever enough to come up with a spontaneous comment. You do have something to say. You’re just dismissing it. So feel, don’t think, and say it. If you censor yourself by thinking about what you’re going to say, you kill the emotion. Passion, excitement and fear are all good emotions to feed off of in telling a good anecdote. If you don’t feel anything while you’re telling it, neither will anyone else. But don’t use anger. People want to laugh at anecdotes or get caught up in the fear or excitement of the story. They do not want to be made angry. And you do not want women to think of you as an angry, negative, complaining person. Telling tales of frustration or embarrassment is fine as long as they come off as funny (see exaggeration above). If you aren’t funny (be honest), or just have a hard time being funny in certain social settings, don’t tell those kinds of anecdotes. Stick to the scary or exciting ones.

Tell the Story in the Right Order. Don’t put yourself in a position where you have to backtrack and explain something or add an event that happened earlier that you now realize you need to tell in order for your story to make sense. It’s like flashbacks in movies. It kills the forward momentum. So before you tell an anecdote, briefly go over the chronology in your head before you start talking. (Okay, so I’m contradicting myself about the not-thinking-before-you-talk rule.)

What do you do if you have trouble coming up with anecdotes? Where do people come up with ideas for anecdotes? From their own lives mostly. You have one of those, don’t you? Start keeping a journal or a blog, if you don’t already, and use it to tell funny and interesting stories from your week. Craft it as you would a fictional story. Decide what emotion you want to elicit and hook the reader.
Writing down your life will help you think of your own life in story terms, and you will begin to notice anecdotes all around you. Right now, think about finding a dime on the street. Think very hard about it. You know the old trick. Now that you’ve thought about it, you’ll start seeing dimes everywhere. It’s the same with anecdotes.

In your pursuit of anecdotes, you may find yourself doing stupid things just to have a story to tell.

I encourage that.

Exercise: Write down a story from your life of the past week. Is the topic something out of the norm or, if it’s about an everyday sort of occurrence, can you tell it in a funny way? What emotion do you feel as you record it? What kind of emotion does the story bring out in the reader?

Next time: How to Change the Topic of Conversation

What to Say (Conversational Skills, Part 5)

So you’ve asked some questions of your conversational partner, but now it’s time for you to do some of the talking. What do you say and how do you prepare?

Just to be sure, a few words of warning:

Do not call her a ‘girl’ because she can’t do certain things (every woman likes to think she’s capable of anything) or similar sexist comments, even if you’re “joking.”

Do not refer to a woman (not just her, but any woman) as a ‘girl.’

If this is your first conversation with her, do not talk about sex--unless she brings it up.

Do not comment on how good looking someone else is (even a movie star) unless you’re referring to a man.

Okay, now on to preparation!

First, you need to be prepared to answer boring and/or embarrassing questions. Most people do not know how to ask questions, so you will often be faced with those vague, generalized questions that I’ve told you not to ask (at least not to ask without an interesting follow up question). So decide beforehand what you will say if someone asks you any of those questions that you hate answering or don’t have a good answer for.

Do normal people pre-plan their answers for social occasions? Likely not. But then most of them are also boring. Don’t let your judgment about how pathetic, stupid, contrived, etc. it is to pre-plan answers get in your way of pre-planning answers! More conversations would be more interesting if people did pre-plan.

What are the questions that get you stuck for an answer or only ever elicit answers that no one listens to or cares about?

Here are some examples:

What have you been up to? What’s new? (or other derivations thereof)

What do you do?

When was your last relationship? (or other derivations thereof)

Now add your own questions to this list. Write out three possible answers to each of these questions that stymie you. Look over your answers. Are they interesting? Do you want to know more? Do they show passion? Do they express an opinion? Do they avoid embarrassing yourself but are still true?

Up on Friday: How to Tell an Anecdote

What to Say (Conversational Skills, Part 4)

Today I continue with some tips on the art of conversation.

Adding on to Tuesdays list of topics of conversation, remember to make mental notes of what acquaintances have told you about their activities and follow up the next time you see them (or later in the evening). Remembering that she had to get lasik eye surgery shows that you care about her as a person. Or saying “I couldn’t help but think of you when I saw [the latest Meg Ryan movie] because you look so much like her (or I remember you saying you really admired her, etc.)” also shows your interest in this person.

Now you think of ten questions to ask a woman you’re interested in. Yes, right now. Get a piece of paper (or open a google doc) and write them down.

Ask yourself: Do you care about the answers to those questions? Would you want to answer those questions? Do your questions bring out conversational meat--do they elicit opinions or strong feelings?

So you’ve asked the question. Now you need to listen. And show that you’re listening. Yes, you can listen while you’re looking something up on Google on your iPhone, but doing so conveys that you’d rather be on the Web than on her. Let your body language show you’re interested:

Maintain eye contact (but don’t stare)

Lean forward

Figure out where to put your hands and leave them there--quit fidgeting. It conveys impatience or nervousness. Neither of which are appealing.

Leave your arms open, not crossed

Nod, and say “umhm”

And pay attention to her body language so you can gauge her interest in the conversation. Interest is shown by: eye dilation, blinking more rapidly than normal, leaning forward, touching you, mirroring your body language and expressive use of the eyebrows.

BUT do not let her do all the talking. Even if she seems really into hearing herself talk on and on, it doesn’t allow her to get to know you at all. It’ll be hard for her to think about you or look forward to seeing you if she doesn’t know anything about you. Yes, she might want to hang out with you because you stroke her ego. But you want more than that. You also want her to be interested in you as a person. If you only listen you come off as boring and/or desperate.

Up next week: Now it's your turn to talk--so what do you say?