The "Three Mistake Minimum" Rule on Dates

I've had a lot of girls ask recently how they can be more "open," more authentic, more vulnerable. They recognize that these dispositions not only allow them to be their true feminine selves, but are also attractive to men in a non-sexual way. This post is for them. If you are the kind of girl who prides herself for "speaking her mind" on dates, this post is not for you. In fact, you probably need to shut up more.

When my friend and I used to go out in San Diego, we would sometimes make a rule at the beginning of the night: no one could go home until they'd approached and been rejected five times by girls. If you were successful and chose to leave the interaction or got a phone number, it didn't count towards the total. Sometimes we would aim for three rejections, other times five rejections, and on ambitious nights we'd shoot for ten. It made for some fun times. The way we saw it, if we weren't getting rejected often, it meant we weren't trying hard enough. More importantly, it made approaching easier. If we knew we had to get rejected ten times anyway, we'd think "might as well get started now." It always worked. What at first seemed like recklessness actually made us successful, because our indifference to rejection gave us the bearing we needed to communicate our confidence; and women ended up liking us more.

As I pointed out in a seemingly unrelated post, taking risks is something we all need to do in order to succeed. We tend to avoid risks because they lead to failure, but risk-taking is also a prerequisite for success. We have to embrace the chance of failure if we want to succeed. This applies to dating as much as every other aspect of our lives. While there are many things we can control to attract the opposite sex, experience shows us that not everything can be manipulated, and there is a point at which we need to let go and accept the limits of our influence.

A lot of women find first dates nerve-racking. Whether or not they realize or admit it, they are nervous because they see a first date as a time to perform, a single opportunity to show their best side to a man, a critical chance to impress him. They are self-conscious because they want to avoid doing something stupid or unattractive. If you are one of these women, you know exactly what I am talking about. It can be paralyzing.

When you are having a conversation on a first date, all kinds of thoughts and reminders are constantly passing through your mind. Some of them seem appropriate and you verbalize them, but many you veto because you aren't sure if he'll agree, or whether he'll be interested. These are things that you would say without a moments' hesitation in front of a work acquaintance or a friend; but you don't want to say something that will turn off your date, or make him think that your tastes or opinions differ too much from his. So you leave these things unsaid.

Example 1 - He mentions a boring, generic Hollywood movie he saw the other day and really liked, and asks what the most recent movie you've seen was. You tell him that it was A Separation. When he asks how you liked it, you balk. You thought it was incredible, the best movie you've seen in years; but you are hesitant to tell him so because you doubt he appreciates foreign (let alone Persian) films, and he might even think you are a little weird because of it. You tell him "It was good... different, but good" and change the subject.

Example 2 -  You met online and it's your first date. He invites you to dinner but doesn't tell you the name of the restaurant ahead of time. You've had a long day so you are hoping for someplace casual where you can just kick back and have a beer with him. When he picks you up he is a lot hotter in-person than you expected. He takes you to a fairly fancy place, and when the waitress comes, he orders a cocktail. You do too, even though you never drink anything other than Bud Light and think cocktails are kind of pretentious.

In both instances you lack authenticity. This kind of guarded, deferential mentality is preventing you from being your true self. More to the point here, it is preventing you from finding a man that is truly compatible with you. I've been on dates with girls that have been very open and genuine, and I've had absolutely no interest in them because of it. They showed their true colors, and I didn't like them. But these girls are far closer to finding a guy than the women I've dated several times without ever feeling like I knew who they were. A few of these girls gave me glimpses of their true selves occasionally, and I loved what I saw. But the glimpses were far too brief and fleeting for me to really know whether it was representative or not - in other words, whether or not it was worth hanging around for. So I didn't.

You probably assume this guarded mentality in order to prevent yourself from failing with men (looking stupid); but it is also preventing you from succeeding with them. The kind of guy who would like what you decided against saying will think less of you for your silence, while the guy who would think poorly of you for it probably isn't right for you anyway. Your attempt to make the date work by avoiding your natural inclinations is futile, because, although your instinct is right - it will prevent you from looking stupid - it will also prevent you from being attractive to the men you are most suited for.

So next time you are on a date, do the equivalent of what my friends and I used to do in the bars of San Diego: do not go home until you've made a conscious effort to push through your reservations and express the things you would say in non-date situations - at least three times. In other words, don't go home until you've made three "mistakes." Remind yourself of this just before meeting him for the date, and then anytime you are alone during it (e.g. when you go to the bathroom). If you want to get hyper-practical about it, set an alert on your phone, so that you get a little vibrate reminder part-way into the date. If you get to the end of the date and still haven't hit three, just ask him anything you want  to know about him but "isn't appropriate" to ask.


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Fifteen Red Flags in The Dating World

While none of the items on this list should be considered conclusive on their own, they all point in varying degrees towards "player" or "he doesn't like you enough," and should be recognized as red flags. Watch out for them.

You can be sure that he isn't interested enough, or that he is just trying to have sex with you, if three or more of the following are true:

1. He only invites you to go out with him to bars/clubs, or other places that involve drinking. If he liked you for more than sexual reasons, he would ask you to hang out with him in a normal environment that gives you an opportunity to get to know each other.

2. He contacts you sporadically, and often goes silent for days on end. If a guy is genuinely interested in you, he will crave interaction with you. As long as you are giving him positive feedback when he contacts you, he will maintain or even escalate the amount of contact. A few guys know a little about "game" so his sporadic texts could actually be a poor attempt at attracting you; but men that use "game" tactics heavily are probably just trying to bang you anyway - so your conclusion will be the same regardless.

3. He is overly protective of his cell phone. For example, if you are looking at a photo, he will get up to stand over your shoulder to make sure you aren't looking through his photo gallery; or he will never let you hold his phone. Unless he has something to hide, there should be nothing wrong whatsoever with you looking through his photos or even his texts. Although you should never look through his phone when he isn't around, it wouldn't be a bad idea to see how he reacts if you try this in his presence (assuming you have reason to be suspicious).

4. He only contacts you by text or online chat. These forms of communication are low-investment because they don't require his devoted attention, leaving him free to do other things - including communicating with other girls. If you have what seem to be deep conversations but they only occur (for example) when he is chatting with you online while he is at the office, you should start to ask yourself questions and keep an eye open for other items on this list.

5. He frequently tries to escalate the relationship sexually, while making little or no efforts to get to know you personally. Guys who are interested in you as a person are probably just as horny as guys who have no desire to spend time with you outside the bedroom. But the guy who is also interested in your personality will curtail his sexual desire in order to avoid giving you the wrong impression.

6. He informs you where he is going, but doesn't invite you. For example, on a Friday night he might text you something like "I am headed to [bar name]" without explicitly inviting you, because his goal is to get you to come to him. This is his filter: if you aren't interested enough to come to him (and therefore more likely to get drunk with him and have sex), he will be free to try his chances with other slutty women.

7. He has never seemed nervous or uncertain around you, even at the beginning when he first approached you. Men who are really interested in a woman for more than her body will be careful about what they say and do around her. They might not be visibly nervous, but neither will they be ostentatious nor cocky.

8. He makes open-ended and non-committal plans with you, like "Let's hang out soon." or "We should get together sometime." Men who want to spend time with you will either have something in mind, or come up with a plan, even if it sucks: "Let's go see the new Disney movie - are you free Thursday night?"

9. He avoids going out to bars and clubs with you because he wants to hit on other girls. Excuses about "guys' night out" or "bro's before ho's" are likely just that - excuses.

10. He goes out to bars and clubs a lot. This is almost self-explanatory. Alcohol is the greatest facilitator of easy sex, and bars and nightclubs - although good places to meet men if you use them correctly - are also the only venues other than brothels that facilitate casual sex.

11. He won't spend his Friday or Saturday nights with you. I can't count the number of times I've avoided dates on weekend nights. Men do this because they want to go out to meet new girls, and Friday and Saturday nights are prime time. For a player, the prospect of something better always looms on the horizon. He is sexually ambitious.

12. He never goes out of his way to hang out with you. For example, he wants to hang out until he finds out that you live far away and then he loses interest or asks you to come to him. Or maybe he wants to watch a routine sports game on the only night you have free, so you have to push the date a week. If (what should be) minor impediments stop him from seeing you, you should be concerned.

13. He tells you that he isn't looking for a relationship. Believe him. It amazes me how many of the women who write to me for advice ignore such a blatant comment.

14. He makes plans with you at the last minute. He does this because he is keeping his options open, waiting for something better or more fun with a hotter girl. Maybe he texts you at 7 pm on Friday "Hey what are you up to tonight?" While rules about making him set up a date three days in advanced are quickly growing antiquated as the pace of life increases, the principle that he should like you enough to plan ahead still holds.

15. He doesn't explain any of the above. It is reasonable to think that some of the things above could happen occasionally for reasons other than his attempts to get other women, or his lack of interest in you. But if this is the case, he will make an effort to explain his behavior in order to maintain his reputation in your eyes.


Related Posts
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How to Reject a Guy

If you aren't swooping up dudes by the dozens you might not give too much thought to this topic, but at some point it will become relevant. Whether you are getting asked by a guy for your phone number, or asked out on a date, or pressured for sex - or even if you are proposed to, if you don't want to say yes, remember the following:

1. He can handle it. At least, he should be able to. Any man who wants to stand even a modest chance of success in the dating world needs to learn how to handle rejection, so don't shy from the task. Your concern for his feelings should never stop you from being up-front with him.

2. He wants to know the truth. He wants to be with you, but only if you reciprocate that feeling. You wouldn't want to be with a guy who was apathetic about you. Likewise, he'd rather know your true feelings than have your insincere acceptance.

3. He doesn't want his time wasted. If you aren't interested, he wants to start looking elsewhere as soon as possible (just as you should).

4. His primary emotion will be anger if you've only just met him or haven't been dating very long. Men take longer than women to get emotionally involved, so in the early stages of a relationship, his pride will be hurt far more than his heart or soul. While women will usually respond to this kind of rejection with sadness, men much more likely to be offended and angered, regardless of how well they hide it. So say what you have to quickly, and get the fuck out of there to let him cool off.

5. There is no way to soften the blow. This is what women (and probably men, too) forget the most when they reject a guy. You're telling him he isn't good enough for you, and that salient point will break through any bullshit you try to pad it with, so don't try. Additions like "I really like you, but..." are unnecessary and only make you sound insincere. The best way to deal with the inevitable is to plow through it as quickly as possible.

6. Most guys will persist at least a little. Don't be surprised or act indignant if he tries to convince you to go out with him, or to give you his number, or to stay with him. Men are rational by nature, and this kind of reasoning works on us, so we assume it will work on you too. Humor his reasoning by politely repeating your reasons (if it is a break up) or simply your refusal (if he is asking for a date or your number).

With that background, you should be able to appreciate the general strategy for rejecting a man, which is to be clear, direct and brief. That is to say, make sure he knows you are rejecting him, suppress the urge to make excuses for why you don't want him, and reject him quickly.

To state the same things in negative terms:

• Don't be vague in an attempt to soften the blow. Make sure he knows that you are saying "no" or breaking up with him.
• Don't make excuses about why you can't give him your number, or go out with him, or date him anymore.
• Don't try to soften the rejection by adding all kinds of caveats or compliments or by "talking it through." If you are ending a relationship there is a good chance he will want to talk about it, probably in attempt to reason with you (see #6 above), but I suggest you avoid this as much as possible. You can always talk to him later after he's had time to think about it.

When it comes to being asked out or called, you do have the option of ignoring his text or call, but this is fairly rude. I do it to girls sometimes, but it is a better all-around policy to answer and follow the guidelines above. If you don't give your number to a guy or lead him on when you don't like him, this probably won't be an issue anyway, since you will be looking forward to hearing from him.


Related Posts
1. How to Reject a Guy at a Bar - Part 1
2. What it Is Like to Be Rejected By Girls
3. Get Used to Rejection
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Never Tell a Man Why He Shouldn't Want to Date You

One of the funniest but wisest quotes I've ever read was from the recent bestselling book & Twitter feed "Shit My Dad Says." The author recounts a time when he was telling his father about a girl he'd just been on a date with. Dejected, he tells his dad that she is obviously out of his league. His dad replies:

"That woman was sexy...Out of your league? Son. Let women figure out why they won't screw you, don't do it for them."

Of course the advice in this specific instance is about sex and women. But encapsulated in his words is a lesson that many people - men and women - painfully need to learn. Regardless of how bad your situation in life is, you should always hold your head high and illustrate or describe your personal situation in the best light possible. There is simply never a need, under any circumstances, to highlight the negative aspects of your life. There will always be external factors working against you - biology, genetics, social stigmas, gossip, etc. You don't need to contribute to them. Never tell a man why he shouldn't want to date you.

I've been dumbfounded at some of the shit women tell me on dates. It reflects so poorly on them, yet they tell it to me voluntarily. I get the impression that they are trying to be "candid" or "unfiltered," but that intention is only appropriate for people who have nothing in their life that needs to be filtered.

Although there are some situations in which it is necessary to do so, as a rule you should never voluntarily talk about or even mention any of the following:

1. Guys that have broken up with you, or any failed relationships
2. Difficulties you have finding a guy
3. How much it sucks being single
4. That you have been raped or physically abused
5. Any bad life experiences you've had (or are having)
6. Family drama (e.g. that your mother despises your father's parents)
7. Your lack of a social life
8. Your dissatisfaction with your current life situation
9. Your struggles with depression, a disability, or being a single mother
10. How much you hate your job

I am not making this list up. I went on a second date with a girl once who spent the whole time telling me about her parents' ongoing divorce, how crazy it was and how she and her siblings kept fighting. Word-by-word, she painted a hugely unattractive picture of her life, and I lost attraction for her because of it. Another time - before we'd even gone on a date - a girl told me she'd been raped by two black men in college (she was trying to disarm a comment I made about her being "innocent"). I never asked her out.

It isn't as if all negative comments need to be purged from your conversation. It is fine to mention small things, like "God, it's so frustrating; the seats of my BMW are taking sooo long to break in..." or "Argh! I hate this cell phone, it is constantly auto-updating." While these kinds of comments might make you seem frivolous, it is better that these are the problems on your mind, rather than your upcoming psychiatric exam or how you can't possibly pay the rent next month. When it comes to big things, keep your mouth shut about anything negative.

If you have serious issues that you think your boyfriend should probably know about, like a serious STD or an alcoholic father, you can and probably should tell him about them - eventually. Bring up the bad things only after he's had a chance to see the positive aspects of your life that outweigh them.

Don't Talk Yourself Up

I've been on a number of first dates, or early dates anyway, during which the girl essentially tried convincing me that she was hot shit. This hasn't typically been outright bragging. In fact, I think in all instances that I can recall, the girl has ostensibly just been telling me about her dating history or personal experiences. But her narrative has been laced with comments about how she is usually the one to end relationships, or how she goes on a lot of first dates, or how she just can't seem to find someone that is intelligent but confident, extroverted but thoughtful, good looking but humble, etc. - all of which imply that she has options with men and is generally amazing. Other girls have talked almost immediately and incessantly about how much they've traveled, or their multiple degrees, or their great jobs. Their underlying message is "See? I am a great catch; you should want to date me." They are talking themselves up.

This doesn't annoy me or turn me off from a girl. As I said, it is usually stated very casually and comes across as factual rather than arrogant or cocky. I've never thought "Wow, this girl is full of herself," or decided that I shouldn't hang out with her again because of it. In most instances I've just listened, and quitely acknowledged that the girl was trying to put her best foot forward. Yet in most cases, after getting to know her, I've been the one to end the relationship and she's been the one trying to hold on. And she's looked stupid because, after coming in with such an obvious "look how great I am" speech, she's been the one to walk away unwanted. When pride comes before the fall it makes you look stupid, even if it isn't your pride that causes the fall.

So next time you are on a first date and trying to impress, consider the following:

1. If you talk yourself up, you are likely to look foolish to the guys that you are most interested in impressing. If you are attracted to them, chances are that they will also turn out to be/do/have the things that you consider "impressive." After initially showing off, you may gradually start to realize that the guy you were showing off for is actually in the same league as you, if not one higher. The frame will flip. Your game will actually work against you, because you will end up looking pathetic for bragging about what (to him) isn't such a big deal.

2. A man will be infinitely more impressed by a girl that reveals herself gradually and naturally, than he will be by one that plays all of her best cards at the outset. Behaving this way is attractive because it demonstrates not only humility, but also security and depth of personality. As a man gradually and naturally learns about your strengths (for example, when they come up in the natural course of conversation, or when he asks you about them), he will get the subtle yet strong impression that you are "bottomless," and that you feel no need to impress him. He will be drawn into your depth and attracted by your confidence.

Who Pays On Dates?

When it comes to paying for dates, the rule is simple: always assume you are going to split the check, and offer to do so. If you wouldn't be willing to pay for your half of the date in order to spend time with a guy, then you shouldn't accept his invitation to go out in the first place. So the first part of keeping the financial side of dates simple is not accepting invitations from guys you aren't interested in.

In most cases, when you offer to pay for yourself, he will refuse. If he doesn't, remember that your assumption was that you were paying for yourself anyway. He is probably just as confused about whether or not he should insist on paying, as you are about whether or not you should offer. Some men think they will offend the woman by offering to pay (by suggesting that she couldn't). Others have probably heard advice saying that they shouldn't so that you won't think he is too interested in you.

When the check arrives or you approach the cashier, always reach for your money. This shouldn't be theatrics or an attempt to induce his offer to pick up the check. Remember, unless he tells you otherwise, assume that you are going to pay for your half and act accordingly. If you get your money out faster than he does or get to the cashier first, ask him "so do you want to just split it?" (i.e. divide it 50-50 rather than itemize). This way he knows you aren't trying to pay for the whole thing. Asking him "can I pay for my half?" before he offers to pay for your half sounds presumptuous because it implies that he was planning to pay for you, when he very well may not have been.

If he refuses your offer to pay for yourself, don't insist. This heightens the confusion for the guy (see above). It also isn't necessary. If he actually wants to split the check he will accept your offer the first time. If he refuses to let you pay, reply with a simple "are you sure?.... thank you" and leave it at that.

If you are short on money and can't afford to pay for yourself (e.g. for an expensive dinner), tell him this when he asks you out. Say something like "I'd really like to but I can't afford to [whatever the date is] right now. Could we go [somewhere else] instead?" (the key is suggesting an alternative). At this point he will probably clarify that he is picking up the check, so all you need to do is politely accept. If he doesn't offer, then you've just avoided an awkward situation in which the time to pay arrives and you don't have enough money to cover your part.

Never offer to pay for the whole date (i.e. pay for him and yourself) until you've been out several times, or received some kind of commitment from him. While it is a generous gesture, it could too easily be interpreted as an attempt to impress. If he sees that you want him badly, he will start to wonder in the back of his mind if he can do better. It might also come off as an assertion of your individuality, which will not impress him. This is something women like in men, not vice versa.

If he pays, make a point to say thank you. While failing to do so probably won't be the only factor in a guy's decision to ask you out again, it can definitely be the straw that breaks the camel's back. Don't fuck up your chances by omitting common courtesy.

In general, stop thinking about dates as formulaic "events" for which Hollywood has defined the normal course and etiquette. A date is nothing other than two people who are attracted to each other spending time together. Neither of you knows the other well enough to be sure that the investment of time and money will be worthwhile, so neither of you owes the other anything - let alone paying for the other.

Clean Up Your Room. And Apartment. And Car...

One time I went back to a girl's studio apartment after going out with some of our mutual friends. I'd met her that night, and was pretty attracted to her until we got to her place: it was filthy. The bathroom was disgusting, her clothes were everywhere, the bed wasn't made and it was poorly decorated. As I stepped through the door and saw the mess, I subconsciously but immediately relegated her to the zone of "girls to bang but not date."

Contrast this with one of my ex-girlfriends, who always kept her place nice. She didn't always have the most expensive stuff, but she put thought into the way it was decorated, took care of her things, and created a living environment that I actually enjoyed being in more than my own. Every time I was there my experience was all the more positive because of the efforts she had made. I couldn't help but associate those positive feelings with her, since I always had them in her presence. On more than one occasion I consciously considered the fact that if we were to ever get married, I would be able to live in that kind of environment for the rest of my life. And while something like that would never make or break my decision to marry a girl, I know that those kinds of background influences play into our gut feelings about a person much more than we usually realize.

Some men can put up with disorganization and uncleanliness more than others, and I would be remiss to hide the fact that I am much closer to the intolerant end of that scale than most. However, consider this for a moment: you won't turn any guy off by being neat, but you will definitely turn off some by being a slob. So play it safe: clean up your shit, paint an accent wall in your place, hang some framed pictures and take the seven pairs of heels out of your car's back seat - it could make a big difference on your next date.

Who Is This Girl?

"Who is this girl??" I thought as she handed me a bottle of wine. I'd only been dating her for a few weeks and we'd probably only gone out a couple times, but here she was, meeting me at the mall to go shopping, and bringing me a gift. My memory is a little vague but I don’t even think we’d slept together at that point, or if so it had only been once or twice.

"My mom and I had a bottle of this the other night with dinner and really liked it. I noticed you had a few bottles of red wines at your apartment, so I brought this for you."

My jaw was basically hanging on the floor at this point. Girls never do this. In fact, I can count on one hand the number of gifts I have received from dates. I could almost feel my opinion of this girl increasing as I experienced some combination of surprise, gratefulness, flattery and – I mean this honestly – sexual arousal. Surprise because it was so unexpected. Gratefulness because I do like red wine, and it was a type she particularly enjoyed so probably it would be good. Flattery because she was demonstrating that she cared enough to think about me when we weren’t together. And then sexual arousal – why? I can’t entirely describe it because I have so few instances to reflect on, but I think by bringing me a gift she was being extremely nurturing and feminine, and that is incredibly sexy. It also made her stand out from other girls just because she was doing something so unheard of.

The act of gift-giving should be used sparingly. As with other demonstrations of affection or appreciation, it is only powerful because it is rare. However, it is also uncommon enough to be missed in many instances when it would be useful. It is an extremely classy, mature and sexy way of telling a guy you are into him, and therefore does not lower a girl’s value by making her seem clingy, the way a random “I’m thinking of you” text would.

Finally, I think it is important that the gift be given casually, and should not be anything valuable. This adds subtlety, and helps maintain a girl’s value. If I were given expensive cologne, it would seem like she was trying too hard, but a bottle of wine is perfect.