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How to Overcome Sexual Issues Present in Younger Women

overcoming sexual issues

Chasing after and bagging a younger woman definitely has it’s advantages. They’re far more likely to be carefree, open to trying new things and lack any relationship-weighing baggage.

But there is one fall back: younger women will typically lack the sexual experience and confidence that you would find in an older woman. However, you can use this to your advantage by serving as the older man who comes in and rocks her world, teachers her a thing or two about sex and ultimately impacts the rest of her sexual life. Sounds pretty great, eh? I thought so.

How do you do it, though? Just sticking it in isn’t going to do the trick. You have to approach this with a certain level of finesse and care. Here are some things you may encounter when dating a younger woman and the ways you can overcome them.

Lacking confidence (physically and mentally)

overcome sexual issuesYounger women are likely to lack a little confidence, whether it be about their body or in the bedroom. It’s gonna take awhile for them to really come into their own after years of digesting magazine covers and media that tells women they have to be perfect. Be aware of this and see if she shys away from keeping the lights on or feels weird about you going down on her (two things you probably want to do!)

You can correct these things by respecting her wishes at first, but then slowly pushing the envelope, while continually fueling her self-esteem. Let her know she’s beautiful and that you want nothing more than to . Persuade her to get naked during the day when turning the lights off isn’t an option. She’ll also become more and more comfortable with being naked the more time she actually spends naked.

Now, it’s important to understand that there is a difference between insecurity and simply not wanting you to do something. Telling you she’s not into anal sex and not wanting you to go down on her can be two very different things. You can work on both of these sexual to-dos, but building her self-esteem may not work for all of them.

Lacking experience (worldly and in the bedroom)

Dating someone who lacks sexual experience can be both a lot of fun and difficult at times. They may be eager to try everything or they could be scared to move beyond missionary. And what’s worse is they could be bad at everything. Most of these problems can be fixed though, no matter the issue.

Use this time to expand your younger counterpart’s sexual vision, but be ready to be patient if they are a little hesitant. You won’t be able to whip out the Adam & Eve products right away, but can slowly ease into them as well as other positions by once again appealing to her self-esteem and reassuring her. Lead by example and take charge, talk a little dirty and move her around a bit. See how she reacts and gauge whether you can dive in or need to progress slowly. Respectful persistence will usually persevere.

If she’s bad at things, take this as your chance to be an educator. Let her know how YOU like certain things to be done. Don’t let her know she is bad, instead position this as a lesson in what you like. In turn, you can ask her how she likes things to be done. The one benefit of this situation is that you’ll be guaranteed some quality bedroom skills once she’s gotten it down.

Stage Five Clinger Status

All women have the capacity to develop Stage Five Clinger Status (just like men), but you are far more likely to encounter this issue with a younger woman. Having sex with them can be the catalyst for this issue, so you have to tread carefully. If you’re trying to date, great, if you’re just trying to hit it and quit it, you need to be careful. You can typically see a Stage Five Clinger from a mile away, they’ll show you in their self-esteem before you’ve even gotten them in bed. If you’re not looking for that, avoid the pump and dump and/or let them know what you’re looking or upfront and be ready to let them know that again and again. Stage Five Clingers can be crazy, so do what you can to avoid them at all costs.

What are some sexual issues you’ve encountered with younger women?

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The Key To Succeeding With Younger Women

Rather than brag about my “rock star” lifestyle (which I don’t actually live), or offering tons of “how-to” advice on meeting younger women, I want to take a different perspective and share my life with you.

I’m not one of those dating gurus who acts like I’m the best seducer in the world, or perfect with women. I’m not. I’m not one to brag about my conquests or try to get you to believe that when I enter a bar, swarms of young women get on their knees and beg to blow me.

What I can share with you is how I have been able to transform myself into a guy who regularly dates and sleeps with younger women.

If you are familiar with my book How to Succeed with Women, you already know a few things about me. I’m Jewish. I’m chubby, and I live in Wisconsin. I’m not a pretty boy, nor am I an amazing dresser. I’m pretty average looking, and have no intention of lying or manipulating women into bed. That goes against my personal code of ethics.

I just turned 40, and I was a bit nervous and bummed out when that day came. It was the end of my 30s—and I was honestly a bit freaked out and worried that my skills with women might somehow decline, or my confidence would be destroyed.

I’m starting to see some grey hairs, and experiences such as my mother dying a few years ago—and a few friends of mine passing away from heart attacks—have made me contemplate the impermanence of life. And it definitely has me realizing that I am no longer 22 and invincible.

How To Succeed With Younger Women

talking to women

But let me back up for a second. I’ve had really good success with women for the past 12 years. I actually remember the day I was with David Copeland (my friend who I wrote How to Succeed with Women with), and we were both pissed off and frustrated that we had no game at all with women. We sucked, frankly, and so we set out to try to figure this stuff out.

We did, to a certain extent, and we related our findings in How to Succeed with Women. I began with absolutely no success, and slowly had more and more success. And as I developed more confidence, I slowly began to date hotter and hotter women. And this made me a happier guy all around.

I’ve also found that over the past three years, as I have felt more secure in my life—in my job, my house, my spirituality, and in my life in general—I  have ceased to worry about my success with women, or be concerned with women at all. Now, they seem to just “show up” in my life without a lot of effort on my part. I say that not to brag, but because I think that it’s more a reflection of the work I’ve done on myself.

That sounds new-agey and all, but it’s true. And it makes sense. The less focused on women you become, the less you feel lonely, needy, and desperate you are. This is when you become open and relaxed. Women feel that vibe, and want to be around that sort of energy.

I met my current girlfriend, who is 26, at a coffee shop. She was working on her laptop and I asked her what she was writing. Not a mind-blowing or complicated approach at all, I know. But it was a genuine question that I asked, mainly because she looked cute and interesting.

As it turned out, she was a writer for a newspaper. I obviously write, too, and we hit it off. I told her about the books I’d written on dating, and we spoke extensively about How to Succeed with Women. I didn’t try to hide it or deny that part of my life. At first she thought I was lying, until I showed her my website. She thought it was amusing, but interesting. I got her phone number, and we texted each other for a while before meeting again.

Approaching Women The Right Way

My approach with her was to be as real as possible. Not to show off, brag, act overly cocky and funny, overly cute, or overly sexual, but to simply be authentic. I talked with her about a huge variety of topics: music, art, gossip about celebrities, her job, and eventually sex and kink. The underlying thing I noticed in our interactions was that we were both genuinely interested in the other person.

How did I turn this sexy 26 year old into a lover? Our first “date” was drinks at a bar, and just hanging out, talking. The conversation at the bar went well, but nothing physical happened until date #2. On that date, we went to a few bars in one part of town and I walked her home. We made out on her steps for a long time and I went home. On the third date we had sex. A funny detail to the sex was that while we were getting it on, a living room full of 23 year olds were playing videos games on a huge TV in the other room. I could hear the sound of the video game in the background as we had sex.

Before her, I dated a 27-year-old chick who was an engineer. She was at a bar, and I asked her about a piece of jewelry she was wearing that looked really cool. Again, not a complicated or cunning approach. We talked about cool places to travel around the world. We ended up talking about Europe and Asia for at least a half hour. She been in Germany recently, and I had been in Europe leading dating  workshops a few months before.

I got her number and we ended up emailing for a while before meeting again. She was really into hiking, and our first bunch of dates involved walking in nature with her dog—and we would make out in the woods.

Meeting And Interacting With Women

Here’s another example of meeting another woman in her 20s. I travel frequently due to my work. Not only do I run dating-related courses and take guys out to bars for “field workshops,” etc., but I also do private coaching and help people publish their books. Last winter I was flying from Chicago to Los Angeles, and luckily I was seated next to a very cool woman in her 20s who was some sort of business consultant. As it turned out, she’s also constantly on the road.

I spotted her when I was in the terminal waiting to board, and I  hoped she was going to sit near me so I could talk to her. As fate would have it, she ended up sitting right next to me. She turned out to be super hot, and really smart.

We began talking about normal bullshit—our jobs, our passions, “travel experiences from hell” stories, and then dating. I asked her to recommend some cool places to check out while I was in Los Angeles. Towards the end of the flight, I suggested that we exchange numbers. While I was in LA, we texted a few times, and finally went out for drinks.

I have many stories of meeting younger women in a variety of places—in clothing stores, coffee shops, and lounges. While traveling and running seminars, on airplanes, on the Internet, on the street in Florida, at personal growth seminars, at parties…lots of places.

I think where you meet women is not that important. Given that younger women are everywhere, it is more about believing you can meet them, and having the balls to approach them.

I’m not super attractive, nor am I particularly “cool.” I honestly don’t think I have extraordinary gifts with women, or innate skills. I believe what helps me out is that I don’t worry about women, nor do I feel fear around them.

When I see a woman who looks interesting to me, I’ve conditioned myself to just talk to her, and find out if she is cool or not. I do have strong conversational skills. I read a lot and know about a wide variety of topics, and truly enjoy getting to know women and learning what they’re all about. And I’m very open about who I am. I don’t hide parts of my personality, my past, or my desires. I’m not a boring and predictable guy.

I’ve been working as a dating coach for over a decade (shit, that makes me feel old!), and most of my clients have been 35+. Lots more have been in the 45-55 age range. What I see them doing often is coming across as what I call a BNB (a Boring Nervous Bonehead). They talk about boring shit, they dress boring, they act in predictable ways…and due to anxiety, they come across more creepy than friendly. In my experience, being boring is the number one thing older guys do to kill their chances of ever dating a younger woman. For more tips on how to date younger women, click here.


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