February 02, 2010


Three Key Dating Mistakes Men Make

I’ve got a special article today from Sheriff, one of our most experienced Love Systems lead instructors.

It’s about dates, and I’d like to cover dates for a few reasons:

  1. The idea of “failing early.” There’s a limit to the amount of time you can spend meeting or hooking up with women. If you mess up your opener, you’ve “lost” maybe a few seconds. But, if you go out, meet someone, talk for a while, do some phone and text game, and then go on a date, and THEN you mess up... that’s hours and hours and hours.

    It follows that dates are the last place you want to mess it up.

  2. Because of this, and because of how long dates take, it’s a lot harder to practice them. You can practice getting attraction from a stranger 20 times in a night, so it’s easier and less costly to learn from your mistakes. You’re probably only going on a couple of dates per week. I want to arm you with as much knowledge about dates as possible.

  3. Pretty much everyone thinks they are better at dates than they actually are. This confused me for a while, but I think I figured it out. Most men are probably decent at dates with the type of woman who normally goes on dates with them. But, that’s not at all the same thing as being good at dates.

Take me as an example. 10 years ago, I had no idea how to meet or attract women, but I got occasional dates. Most of the time, these were with women who knew I didn’t have much “game.” [They weren’t getting many other offers, they knew me for so long that they got past my awkwardness, etc.] In other words, the type of woman I was getting dates with wasn’t expecting me to be very smooth.

But, most men don’t want to date only women who are lonely or have known you for some time. They learn Love Systems, go out, meet more and higher-quality women than before, get good at the first meetings, go on dates, and...

... flop.

In other words, if you want to be the chooser instead of the chosen, work on your dating skills.

That’s why I’m glad to see Sheriff’s article. It covers a couple of the most basic mistakes guys make. There’s much more detail in Chapter 16 on dates in the book Magic Bullets or in the interview series volume with Future and Ajax. So, for a lot of you, this’ll be a review.

3 Key Dating Mistakes

By Sheriff

One of my strengths has always been: give me an evening alone with a girl who likes me - even if she only likes me a little bit - and I'll convert that into something physical. The woman who I'm seeing at the moment broke a string of 23 first-dates that ended in sex.

Every Love Systems instructor has a unique specialty. Mine is dates. A date is a chance for you and a girl to get to know each other, and if you like each other, a great chance to get the awkwardness out of future interactions by taking her to bed.

Being great at dates is about as much work as being great at pickup. And, like pickup, there are a few basic horrible mistakes you can make that are hard to come back from. Avoiding these won’t make you great, but will save you from the worst problems.

1. Not Meeting Her Close to Where You Want To End Up

Women hate awkwardness. And they also hate doing anything that makes them feel too easy, or obligated to have sex. That's why when a woman is coming home with you, she'll often say "We're not having sex tonight!" Just smile, say okay, and know your odds are actually pretty good.

But, if you've met her on a date at an art gallery 20 miles away from your house, how are you going to get her back to your place afterwards? Anything that looks like effort is going to put up her "don't be too easy" defenses - any plan that she makes that she can't easily change again is going to make her back down - such as you driving her to your place in the middle of the night.

If you want to make this easy for yourself, get women to meet you close to your house. If you've made the effort to move somewhere exciting, this will be easy - it should be full of fun bars and cafes. If not, you may have to make do with the local dive bar.

If you want to get the first night's sex out of the way quickly, meet her at a place where the transition back to your place for "one last glass of wine" won't seem contrived, or like one of you is expending a lot of effort to make it happen.

2. Choosing Really Bad Dates Where You Can’t Interact

If a woman is coming on a date with you, she already likes you. What needs to happen next is the two of your need to talk, connect, build some tension, and make it happen.

Don't take her to watch a movie. Invite her over to watch a DVD on your couch with a blanket and a bottle of wine, where you can discuss and interrupt the movie. Sitting next to her in a crowded movie theater for 2 hours? How's that going to help?

Many guys seem to approach their dates from a "make sure nothing goes wrong!" point of view. They're just waiting out their time from meeting the girl to a sensible time for her to invite herself in, and hoping it happens. It rarely does.

3. Pressuring For Sex/Escalating Badly

Women love sex, but they hate feeling bad about having had sex. Preventing that is up to you. Women don’t want to seem too easy or feel obligated. Yet somehow, you still need to guide them into your house, onto the sofa next to you, and make it happen.

For this reason, she needs to be able to maintain plausible deniability the whole time, from meeting you right up to getting her clothes off. It needs to "just happen."

This is largely a function of framing.

But for now, here are three things you can do:

  • Have a good reason you're going back to your place - for me, the old standby was "I've got this great bottle of wine and I'm resenting paying $10 a glass here!" When I was living with my parents, I'd say to girls "I don't want to get a taxi home - do you have a sofa I can crash on?" We're looking for vaguely plausible reasons here, rather than water-tight...

  • Throw in a little disqualifier as you escalate. For example: "Okay, you can see my bedroom, but no sex tonight! I'm on my period," used to work well for me. Also excellent are "I'm putting you in a taxi at 11pm on the dot, so don't be disappointed!" and "It's okay, you can crash. I have the world's biggest bed; it has a barrier you can put up in the middle."

  • Set a frame about her staying over, but nothing will happen. Some women are just shy. Giving them a shirt of yours to sleep in, snuggling under the duvet, and turning the lights off are a magical combination. Turns out it's very easy for something to “Just Happen” in situations like that. :-)

Guys, dates should be a lot of fun, and you're able to control a lot of factors in them. Remember to pull the trigger, and have a think about if you're making any of the mistakes above!

Learn more about Sheriff on his bio.

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Bill Quaintance
Bill Quaintance


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