Hey Dean,

I am 34 years old, from Norway, and I messed things up with a girl I like.

I know your advice is probably to move on and meet new people, but I live in a small town, and there aren’t many high-class women available. After a 6-year relationship, involving 2 kids and a bad breakup, I’ve been single for more than 4 years.

I’ve met many girls since then, but none that I really liked, so I haven’t gotten serious with any of them.

Then I met this girl. 20 years old, from the next city. About a one-hour drive away from me. We hit it off quite well from the start, and on the first night we met we were already kissing, and she spent the night.

She then told me she thought I was a bit old, and things cooled down. But still, we exchanged phone numbers and emails, so we kept in touch, also through Yahoo Messenger. We spent hours and hours chatting, and then she invited me there for the weekend. So, I went there, and we had a great time, but nothing more happened. I NOW know what I did wrong. I was being too friendly, and not like I would have done things now. But still, this increased our contact, and we decided to take a trip together with a couple who are mutual friends of ours. 

In the time between this decision and the trip (a couple of months) we met once a week, and tension was increasing. Physical contact increased, but no sex. But I was being patient, and the weekend of the trip, patience paid off.

Finally. So I must have done something right! And also after we came back. Until a couple of weeks ago….

I felt things were going great, so I told her that I thought we should take things to the next level and make commitments to each other. And that’s when it went all wrong. She was unsure, and instead of cooling down, I pushed on. Trying to logically convince her that this was meant to be, and so on. The classic mistakes. And when she wouldn’t agree, I reacted with frustration, and pulled out.

After a couple of weeks of silence, I made contact with her, and asked what would happen now. She is unsure whether she wants to walk down this path again. But the problem (for me) is that I have never met a girl things were going so naturally with, and I don’t want to lose contact with her. I know making up for this will not be an easy task, but I am prepared to give it another shot.

I am still convinced I will be able to renew contact with her, and when I do, I will use everything I have learnt from your classes, and not fall back to the wuss and needy idiot I have been.

But I still need some advice. Is there anything I must avoid (apart from what I have said I know I have to avoid), and are there any great tips or hints you can give me? I am prepared to give her my best side all the time, being positive and confident, and giving her the same positive experiences I gave her in the beginning.

I don’t want this to end. But on the other hand, I can’t force her, because then the game starts all over again. I’m NOT giving this up.

Like I said, I live in a small town, and I just can’t pick girls like I want. Cards have to be played differently here. I really hope you have some wise words for me.

Best regards,
Frustrated in Norway

* * * * *

First off, I want to commend this guy’s sincerity and honesty. I felt it in his words. Now I’m going to bring some nuclear-powered knowledge to help him get this situation on track…and get this girl back in his arms.

Before I get into that, my friend in Norway, I’m going to need to smack you around a little bit. As I read your email, I spotted several “red flags”—tactical mistakes you made that you must not repeat with this girl again, or make with any girl in the future.

I know you’re aware of some of the mistakes you made, but I know a LOTof guys will benefit from this analysis.

Among the guys that I’ve coached, this is a situation I see all the time. They learn the correct strategies and adopt the right mental attitude…but only temporarily. As soon as they meet that “perfect girl” and sleep with her, they return to their old ways because they don’t want to lose her.

The irony is, by being “super nice,” always being available to talk to her, and making it clear that you want her to be your girlfriend, you are letting her slip away—because her attraction you is decreasing.

Let me run down the red flags in your letter:

#1. After she spent the night with you for the first time, she mentioned to you that you might be “too old” for her. (You are 34, and she is 20.) Incidentally, I’m 34 years old right now, and I tend to date women that are 10 years younger than me (or more), so I’ve learned how to handle this exact situation.

I’m guessing that the age difference was something you were concerned about from the very beginning. You were psyched to meet a cute 20-year-old, but you were probably worried that she would “realize” that you were too old for her.

This is easily avoided. Here are two points to remember when you meet a younger woman:

#1. Never try to conceal your age, and never express any concerns about you being older. Bring it out into the open right away, and USE your age as a way to make her want to prove herself to you. She should be the one who is worried she is not on your intellectual level.

Once she tells you her age, you say, “Wow, I’m 34 years old and you’re only 20? I’ve usually dated women that are closer to my own age. I like women that are sophisticated and have some life experience.”

Wow. That’s an extremely confident, direct thing to say to a young woman. It’s not arrogant or offensive. It shows you have HIGH STANDARDS with the women you date.

Can she measure up to your standards? Well, now is her chance to show you.

You didn’t say, “I can’t date you, you’re too young and inexperienced.”

You said, “I date women who are sophisticated and experienced.”

So, if she wants to hang out with you, she’s going to need to demonstrate that she has these qualities.

You’ve put a CHALLENGE out there, and women get turned on by a man who challenges them to step up!

Now, throw her a question and make her prove that she can hang with a sophisticated guy like you: “But I have to admit, you do seem kind of mature for your age. So tell me some of the things you’re into.”

This is so powerful on a psychological level. Right from the beginning, you’re establishing that you have no insecurity at all about your age; you love being your age, because it means you’re at a secure, confident, experienced stage in your life.

You know about all kinds of cool and interesting things. The only question is, is SHE worthy of hanging out with a guy like you?

#2. Turn your age into a reason for her to want to date you. As an older guy, you’re more worldly and experienced. You can teach her things. You can show her cool places, turn her on to great music, movies, art…whatever your interests are.

I’ll say things to her like, “Last night one of my favorite movies was on television, The Godfather. It’s a classic. You’ve seen it, right?” (This can be any movie released prior to 1985 that you love.)

If she tells you that she has seen the movie, you say: “Wow, I guess I underestimated you. I figured you wouldn’t be aware of any movies prior to Johnny Depp and Brad Pitt coming on the scene.”

If she tells you she hasn’t seen it (and she probably hasn’t), bust on her a little. Say playfully, “I can’t believe you haven’t seen Raging Bull! Wow, there are a lot of things I’m going to need to teach you about…this could take awhile.”

Either way, you’re framing yourself as the older, more experienced MAN who can bring value to her life. Very powerful! (Do you think the typical guy her own age has anything of value to say, or teach her?)

As one of the most often-quoted dating experts in the country for the last ten years, David Wygant has been prominently featured and consulted by thousands of media outlets. He has appeared on E! Entertainment Television, FoxNews, Dateline NBC, CBS News, ABC News and MTV. He has also appeared on over 2,000 radio shows. 

David has been featured and quoted in over 100 magazine and newspaper articles including in Cosmopolitan, Men’s Health, The New York Times, The Chicago Tribune, USA Today, and The Los Angeles Times.  David is one of the leading writers for Yahoo! Personals, and is one of the only dating coaches who works with both men and women. He offers an array of products and coaching services which can be found on his website. David’s website also includes a daily blog for both men and women, along with daily video blogs and podcasts. 

Click here for Part 1…

So what do younger women then look for in an older man?

Experience. It’s your life experience that works to your advantage. For example, you’ve got to really be a great lover, when it comes down to it. If you’re a shitty lover and you’re in your 40s, well, she’s already had shitty lovers because she is used to dating younger guys. I tell every guy I work with to go take tantric sex classes, and really learn how to please a woman.

Secondly, teasing a young woman, which older guys don’t do, is a must. A lot of younger guys go out with a younger woman, and try to sleep with them on the first date. I always tell guys to play it cool and act like you got laid the night before, and look at her at the end of the date and say, “Alright, see you later. Goodbye.” Do it with a smile and tease her. It’s going to drive her up the wall. Don’t touch her for the first few dates, because then she’s going to want to have sex with you. She’s going to wonder why the hell you haven’t touched her. She is going to think you don’t desire her, and then basically throw herself on you. I’m talking about understanding how younger women are wired, but also playing the part.  You’ve got to understand what a young man is like, and act the exact opposite.

In terms of your age and wisdom, don’t try to teach them lessons. Share things with them. Don’t talk down to them; don’t try to give them advice. Encourage them, and share your wisdom and knowledge, because you have to become Michael Douglas. You’ve got to become Sean Connery. You’ve got to become George Clooney. You’ve got to become that cool, hip, older guy that will attract women. You’ve got to be it, before you are it.

Are there tips or techniques you teach your guys on adjusting themselves to the age difference?

Once again, you’ve got to speak with them and speak their language. Be open to what they want to do, but take them on an adventure that the young guys can’t pull off. I’m not talking about buying them a great dinner. I’m talking about being a man with a plan. Meaning, when you go out with them, don’t just take them out to dinner—anyone can do that. Show them that you are fun and playful.

One of my favorite things to do with women is to take them to Target (the big discount department stores). When we’re about to go get a drink, I tell them that first, I need to run a quick errand at Target. When we get there, I give her 13 dimes and nine pennies. So I give her $1.39 and say, “Have you had a treasure hunt yet?” You want to show her that you are not stogy; you are not old. You want to convey a youthful energy about you. So you give her the $1.39, and then you give her the rules: she gets to go on a treasure hunt and she can buy whatever she wants for $1.39, but it has to be one item and one item only. She will canvas Target, looking everywhere! She’ll probably even try to negotiate another five cents out of you, and then you tell her again that the item can only be $1.39, and that’s it. You are willing to pay the tax, but it can only be retail value of $1.39. It’s a fun little game to play. The idea is to behave in the opposite way of the typical older guy, who’s uptight and acts according to the typical script on a date.

Let’s say it’s the summer time; you take her to the park with the Frisbee. Do things that are young and fun. Have a barbeque at your house. You’re not acting old. You’ve got the wisdom and success of a 45 year old man, but by doing those fun things you become someone who she never may have imagined she would go out with. When your life is hip and cool, she wants to hang with that. And when you do those things, you create attraction.

Where do you recommend guys go to meet younger women, and are there locations they should avoid?

I tell guys all the time, “Be the story, not the cliché.” Meaning, you need to create a “romantic comedy.” All women wants to be swept off their feet, whether they know it or not. So you have to be that guy who sweeps women off their feet. So, go out, approach her, learn how to speak her language. Forget about nightclubs and bars. When you’re in the supermarket, coffee shop or anywhere else, approach women very nonchalantly and casually.  Tease her a little bit about the coffee she’s drinking. Tease her about something she is doing.

Here’s one of my favorite openers to use in a grocery store. I’ll see a woman buying a pint of ice cream, for example. I like to walk over and look at the ice cream, open the freezer, and then draw a tic-tac-toe board. Then I put an “X” in the middle and then I say, “It’s your turn, I’ll play you tic-tac-toe for that ice cream.” So all of a sudden it becomes something playful. Then you start describing and talking about ice cream. Tease her and say, “Y’know, ice cream girl,  we need to get together sometime. I have some great chocolate ice cream to show you.” When you call her up, call her “ice cream girl.” She’s already texted all her friends about it, and to them, you’re “ice cream guy.”

So you need to meet her in a playful way. Everyday encounters like that one will beat meeting girls at bars and nightclubs any day of the week.

Are there unique ways to close the deal with younger women, especially if there is a big age gap? Are younger women more suspicious than older women?

I don’t think younger women are more suspicious at all. I think they want to meet someone, but they are suspicious if a man stares, lingers, and acts like a stalker. If a guy has no game at all and approaches with some pickup line, she is going to look at you and think you are an old guy with a cheesy pickup line.

Younger women are looking for sophistication. Most younger women who are willing to date older guys are looking for a guy who is able to teach them things. They are looking for someone who is interesting and sophisticated. If you’re in a coffee shop you say, “I can’t believe you’re not getting the French roast. The French roast they have is amazing.” Then start sharing a story or an experience about it, and then ask her which type of coffee she likes best. Ask her questions and share stories about yourself. Most young guys do not ask enough questions when they flirt. They mostly just use routines. If you’re asking her questions and sharing about yourself, you’re intriguing her in all kinds of different ways.

What advice do you have on managing relationships with younger women?

There is a lot of management in any relationship. You are going to have to realize that everything you went through 20 years ago, you’re going to have to go through again with a younger girlfriend. No matter what you say, you cannot act like you know it all, because she is still going to have to experience it for herself and go through her drama. You’re going to have to listen to shit about her friends, because women in their 20s are always going through dramatic shit with their friends. She’s going to cry one night because she thinks one of her friends doesn’t like her anymore and blah, blah, blah…and you’re going to have to sit there and listen to it, and not offer advice. You just say, “I totally understand, hun,” and let her vent. Then she’s going to feel like you are the only one in the world who understands her, because everyone else is trying to fix her. That shit is going to come at you on a regular basis. You need to be prepared and ready for it. Not only that, but she is going to be more emotional than women in their 30s are. She’s going to get more jealous. You’re going to have to manage that relationship, and spend more effort than you would managing things with a woman your own age. That’s just the reality.

As one of the most often-quoted dating experts in the country for the last ten years, David Wygant has been prominently featured and consulted by thousands of media outlets. He has appeared on E! Entertainment Television, FoxNews, Dateline NBC, CBS News, ABC News and MTV. He has also appeared on over 2,000 radio shows. 

David has been featured and quoted in over 100 magazine and newspaper articles including in Cosmopolitan, Men’s Health, The New York Times, The Chicago Tribune, USA Today, and The Los Angeles Times.  David is one of the leading writers for Yahoo! Personals, and is one of the only dating coaches who works with both men and women. He offers an array of products and coaching services which can be found on his website. David’s website also includes a daily blog for both men and women, along with daily video blogs and podcasts. 

I’m happy today to be talking to David Wygant about how to approach and meet younger women. When I think of you, David, I think of that MTV show you were on called “Made.” You were also on another other show I was on, called” Sex 2K”… that was actually my first exposure to you, and your teachings.

I started in 1998. You and me, we’re the veterans (laughs)…

So how did you get into this field and start doing this?

It’s funny; it’s something that I always wanted to do. I used to make jokes about it to friends of mine back in the early 90’s. I was married, and then divorced, and I would go to bars and I was just not in the mood to be “that guy”—you know, the guy standing around in a bar trying to talk to women. I thought to myself, there must be a better way, and so I started meeting women out and about. I’m not a bar person to begin with, and I don’t particularly like it or enjoy it. I just don’t think there are any redeeming qualities to sitting back and sucking down alcohol all night, because I’m a non-drinker.

So, I started going shopping and doing things I like, and using it as a means to meet women. Then, when I moved toLos Angelesin 1998, a group of guys started following me around all the time because they wanted to learn how I was doing it. It was like “David’s Bootcamp.”  They were all successful, smart guys, but they just weren’t good at one side of their life. That’s how I started in this field. It was something I really enjoyed and understood, and I worked really hard on myself to take it to the next level. It became this great business, and now it’s what I do.

Do older guys often tap your brain about how to meet younger women?

I get asked about this a lot. There are a lot of older guys out there who have not had much experience with younger women, but they want to get into the game. I tell them, if you’re going to play with younger women, you need to start by understanding their psychology.

How do you explain the “younger woman psychology?”

The psychology of younger women is what I call “the little kitten and the string.” Don’t give them everything. The more you ignore them, the more you tease and tantalize them, the more they want you. The problem with a lot of older guys is they try to “buy” younger women. If you “buy” her—taking her to great places, paying for expensive dinners, and constantly doing things for her, you’re basically going to become her sugar daddy. She’s not going to have great, wild, crazy sex with her sugar daddy. She’s going to have great, crazy, wild sex with her lover.

And the only way you are going to become her lover is to learn the art of teasing her, ignoring her, and absolutely busting her every chance you can get. Because she wants what she cannot have.

You have to learn that concept. (The same as when you dangle a string in front of a kitten. As long as you keep the string out of reach, the kitten will go crazy trying to get ahold of it; when you drop the string into the kitten’s paws, it loses interest in about three seconds.)

A lot of older guys just don’t get it. They overdo it on the gifts and the dinners and the trips, and you’re basically just buying a woman who will have sex with you for about three minutes and that’s it. It’s not worth it.

That’s true. It’s like a lot of older men put younger women on a pedestal—viewing them as the golden prize they have to spend all their time and money on. They might also realize there’s a downside to dating younger women, especially the immature ones…

Yes, there can definitely be a downside if she’s not mature. You’re going to get a woman who is going through the dramatic stages of her life, so she’s going to be very inconsistent with her emotions, and what she wants. Older guys think that sex with a younger woman is going to be wild and crazy, but it’s might actually not going to be that way. You might have much better sex with a woman who is over 30.  Some younger women are going to be crazy one night, and then not sleep with you the next night because she still has guilt issues that are left over from childhood.

Secondly, she may have unrealistic views of the world because she has not experienced life. Sometimes the stuff that comes out their mouths makes me scratch my head. But in a lot of cases, when I was their age, I used to think that way, too.

Look, some guys just want young women. They want that hot young piece of ass. It validates them. It makes them feel good. They never had it before, so they put up with the bad parts. Personally, I don’t date women under the age of 30 and I’m 45. I’ve traveled the world and have run five successful businesses.

I work hard. In my case, I don’t feel that a woman under the age of 30 is going to understand me, and I don’t want to go back in time. But I’ve coached a lot of men my age who wanted to date women in their 20’s, and it’s not a tough thing to teach.

You mentioned earlier that many older guys default into buying younger women gifts, spending a lot of money, becoming a sugar daddy…what are some of the other ways they make mistakes in dating younger women?

They don’t look cool. They look like dorks. The fact is, they don’t dress, hip, fun, or trendy at all. If you are going to get a young girl, you better dress the part. You don’t wear your high-waisted jeans or your Dockers to go meet them. You don’t want to look like a nerdy accountant. Instead, you want to look like the business guy who is a rock star on the weekends. You want to dress the role. You want to be that person before you go out.

For me, I can attract women of all ages a 23 year old or whatever, with no problem—because I have a complete image that I’ve created. My image is based on confidence, attitude, and knowledge, and I dress the part. I dress hip, young, and fun. The problem with most guys, especially men over 40, is that they don’t do enough work on themselves. They are not hip, young, or cool, but they want the young tail. If you’re going to go after the young women, you better know how to dress the part, and speak the language of the part, and walk the part, and talk the part.

It’s not about your wallet; it’s about your game. It’s marketing. You need to learn how to market yourself properly to get to the young women. It’s funny to me to see older guys who just got off the golf course go up and hit on a young, hot woman, and all she’s picturing is one of her Dad’s friends who just came from the golf course.

 I get this question all the time:

“I used my opener, she responded, what do I do next?”

Obviously, the general answer to this is: the Transition phase.

The specific answer to “what kind of Transition?” is often a cold read. A cold read is where you tell someone something about themselves that rings true to them, even without any particular knowledge about the person. As you may know from my book Magic Bullets, cold reads are one of the four major types of Transitions. It’s my favorite type of Transition, and I use cold reads in about 90% of my approaches.

Cold reads are one of the easiest techniques to develop, because women will give you instant feedback. When you tell a woman about herself, she will react and give cues to how well your description “fits.”

Over time, you will get better and better at finding good universal cold reads. You will also get better at calibrating your cold reads to take educated guesses about a woman’s personality based on her looks, clothes, mannerisms, and voice.

Sample Cold Read: The Eye Angle Transition

Here’s an example of a good cold read Transition when you meet a woman. This routine works on the theory that eyes that are slanted downwards come across as caring and empathetic, whereas eyes slanted upwards convey a more sincere but fierce impression.

You can use this routine at any point during your opener; even interrupt her at any time to start this one.

“That’s really interesting.”

(She responds.)

“Did you know that if your eyes slant downwards your first impression tends to be empathetic and approachable whereas if your eyes slant upwards people tend to think you’re fierce and unapproachable?”

There are two options from here:

If her eyes slant down “Do you find that people are generally friendly towards you but you really only let a select group of people become really close to you?”

Or:

If her eyes slant up – “Do you find that people don’t always open up to you straight away and you only let a select group of people become really close to you anyway?”

 (She responds.)

“Yeah, you seem like the sort of person that enjoys having friends but only lets a few people into the inner circle. I’m the same way.”

There’s nothing magical about this routine, but it’s a good way of interrupting a conversation that stemmed from your opening line and turning to topics that are of particular interest to beautiful women herself, how she comes across to others, what she is really like, etc. It also implies that you understand her world.

How she can actually be a nice person but because she is beautiful she has had to be less open at first to people because they often have an agenda or preconception about her. You’re already on your way to demonstrating value, which you know from Magic Bullets is the key currency of attraction.