Tag Archives: Dates

How To Dress On A Date

The trick to dressing well on a date is to combine good style and making it look like you didn’t over think it.

I would be pleased to over think it for you, so that you don’t have to.

I think it goes without saying that it is best to wear clothes that flatter you and fit well. Show off your good assets.

Make sure you comb your hair too. My last significant girlfriend told me that she thought I had nice hair while we were on our first date.

Oh, and while we are on the subject, make sure you take some breath mints.

…Alright, back on track.

Another thing to make sure of is that your clothes are comfortable. This serves two purposes. First, you will be comfortable doing whatever it is you end up doing. Second, when your clothes are more comfortable, it helps you feel more comfortable being with this new woman.

The last thing that should guide your decision of what to wear should be that you feel like you look good wearing whatever it is you wear. It doesn’t have to be flashy or exciting, but you should feel like you look good in the clothes you decide to wear on a date. Your dates will go better when you feel sexy and attractive.

Here are some more guidelines that you may consider following beyond these basic rules.

Show different sides of your personality.

If I meet a woman out at a bar, and I am dressed casually, or dressed looking like a rocker in my leather jacket, I often plan the first date for some evening after work, when I will be dressed in a suit and tie. I like to show, with my clothing and style, different aspects of my personality.

This is similar to what I wrote yesterday about wearing accessories that are out of place with your overall look.

There is more to who I am than one particular stereotype, and I want to convey that with the clothes I choose to wear. At this time, I am working to convey breadth of character (depth comes later).

Not many people are always the same person all the time. We vary, sometimes we are fancy, sometimes casual, sometimes upbeat, sometimes mellow, sometimes professional, sometimes sporty, and sometimes slackers.

You can communicate this by wearing a different style of clothing on your date than you did when you met her.

Dress with a goal in mind.

On most first dates, I have a very specific goal in mind. I want to get to know the woman well, and to let her get to know me well. I want to build a connection quickly. I want us to feel like we know each other better after 1 date than she did the last guy after 10 dates.

With this in mind, I often tone down how I dress. I don’t dress as fancy or as flashy as when I met her. I want to communicate that this time together will not entirely be about flash and fun, but about substance.

By toning down my dress, I mean less accessories, less hip, fashionable clothing, less elaborate shoes (not less *nice* shoes though). Essentially, I shift away from dressing like one of the extremes of any stereotype.

Of course, this tactic fits into my overall goal of building a strong connection and rapport on that date. If you have other goals in mind, you can probably think about how you can dress to help communicate those goals.

Style is Communication

You may have noticed that pretty much everything I have written about style this week comes from the perspective of how to communicate to other people with your style.

Clothing and style is a *big* part of the non-verbal communication that we put out in to the world for everyone else to see and understand. No matter what we wear and how we wear it, we are communicating to women something about ourselves.

For a complete dose of learning about the language of style, get Dress For Success. It is a set of DVDs that goes in depth into style, and how it communicates with women.

Dress For Success costs less than a nice pair of jeans and shoes, and you will never buy the wrong jeans or wrong shoes again after watching this program.

Lance, who put this program together, offers a money back guarantee on the DVD program. You’ve got 6 weeks to try it out, and if it isn’t the right thing for you, you can return it for a refund. You’ve got nothing to lose. Except maybe your old crappy clothes.

Click here to go to the PickUp 101 website and get Dress For Success.

Should You Pay For A Woman On A Date?




There is tons of advice on this that floats around our information heavy day and age. I heard someone mention the advice that Tom Leykis gives, to not buy anything for a woman. He says that we are just perpetuating a culture of women that think they should have everything handed to them on a silver platter.

A lot of guys listen. They can see the points that he makes, and feel that they shouldn’t pay for a woman on a date. It’s time to show women that they can’t just take you for a ride.

I disagree, and follow the general rule that if I invite a girl out, I expect to pay.

Maybe you don’t think you should pay for a woman on a date. Now, you can keep on not paying for dates, that’s fine.

Realize that you are going to lose girls that you otherwise wouldn’t have by doing this. I did it too. My head was full of thoughts like “don’t ever pay for women” when I started to learn how to be better with women. And I lost girls that I other wise wouldn’t have. It comes with the territory, so be aware of that. It may be unfortunate, but screaming at a wall won’t make the wall go away.

The thing to realize though, is that spending money during a date for a girl, whether it’s a $3 ice cream cone, or a $10 sandwich, isn’t that big a deal. Objectively, I mean. Even if you are making minimum wage, it still is only half hour to a couple hours of work. In the grand scheme of things, and purely from an objective point of view, there is no big deal with this.

There’s something else going on here with guys that think this. Something that makes spending money on a woman seem like a bad idea. Now, there are way too many men in the world who are sad, hurt, and frustrated because of women. There are way too many men that feel like they can’t get the happiness they want with women. I was this way for years. It didn’t feel good. I felt powerless to get the thing I needed most.

I haven’t listened to very many of the shows that promote this attitude towards women and dating. That is mainly because when I have listened to them, I thought they were total garbage. What they do is give men a way to take all the pain, sadness and frustration they feel, and replace it with anger. It works well for them, because anger is much easier to live with than pain and sadness.

There is another way though, and it is often a bit more difficult. It takes a lot of work, and sometimes requires that men revisit the pain that they have because of their relations and interactions with women so far in their life.

When a man chooses this other way, he takes the pain, sadness, and frustration that he has had, and replaces it with fun, excitement, and happiness as he moves forward. It is a bit harder, but in my experience, it is far better. This is the way that we teach at PickUp 101.

The first step is to learn how to make a woman happy. Check out the program, Everything You Know About Women Is Wrong. It is a great place to start to make the changes, and follow the path to a happier life.

Click here now to find out more.

He's Pushing Her Away From a Relationship

Last night I talked to a close friend of mine. She wanted some advice about a guy she was dating. They met about three weeks ago on match.com. He’s pushing for a committed, serious relationship. After three weeks.

She is about to run away.

The frustrating thing is that she likes this guy, but he is being very pushy. I know he is probably well intentioned too, he’s not just a prick. At least, not intentionally.

My friend deserves the best. She is cute, sexy, fun, loving, giving, empathetic, and, did I mention, cute and sexy? She would probably really like a relationship with this guy, if he would just RELAX.

What is happening is that he is trying to get her to commit to a relationship, but this is totally the wrong thing to do. I think I know what is going on in his head. He met a really cute girl on match, and now he feels like he has to get her committed as soon as possible so he doesn’t lose her. He probably feels like this is about as good as a girl as he could get, or possibly maybe even a little better than he thinks he can get (he’s probably right).

He is making two mistakes.

First, he is being way too pushy, and expecting way more commitment than is appropriate given the ACTUAL level of involvement they have together. This is pushing her away, and if he keeps it up, he is never gonna get her.

Second, he is wrongfully thinking that once he gets her “commitment” to a relationship, then everything is nice and settled. Way too many people get complacent when they are in relationships.

When a man is in a relationship with a woman, he should constantly be building attraction and building intimacy. Let the amount of attraction and intimacy define the relationship, not some sort of agreement.

Ultimately what this guy needs to do is relax, and give my friend some space to let them get closer over time, not to force it do to his poor ability to create a relationship.

In the end, I gave my friend two course of action that she could follow:

1. Break it off now with this guy, because this kind of behavior is really a red flag. If he is pushy and can’t understand her and the relationship now, how will he understand her in a month? A year?

2. Stay in the relationship, but stick to her guns about the level of commitment she wanted, and tell him he can take it or leave it. Even if it ends badly, she will benefit from the experience and knowledge about men that she will gain from dating this guy.

I wish her the best.

And to you reading this, don’t be like this guy.

The Futility of Field Reports

I have a couple of dates this week, and I was thinking about writing field reports about how I met these girls, and I realized that I didn’t have much to write.

For the one I am meeting tonight, the field report would look like this:

“There was a girl outside of the Fort Mason building where the AoR workshop was last weekend, so I started talking to her. We were hanging out for the next few hours, then I suggested a date and she gave me her contact info.”

For the one I am meeting on Friday, the field report would look like this:

“I was out with a bunch of friends for a pub crawl, and towards the end of the night I started talking to this one girl I hadn’t talked to yet, and she was cool, then I set up a date and got her number.”

The point here is that I don’t remember what I said, or what techniques I used, it just kind of flowed. This is the way it should be, and the way it is when all the things we teach in Art of Attraction and Art of Rapport become real behaviors, rather than just specific tactics.