Do You Really Want Dating to Be Easier?

Dating isn't easy. In fact, for anyone with romantic ambitions, it is extremely difficult. There was a time where dating options were far more limited by religion, geography, social class, and family pressure. But these days, dating options are virtually limitless, and ideals about romance are pegged to ridiculous standards, both of which make it hard for people to settle down. When you consider this in light of the fact that people have such varied tastes, it isn't hard to see why it is so difficult to fall mutually in love.

The greatest victories in sports are the ones that follow a difficult comeback. We appreciate them because they are born out of unlikely circumstances, and are the result of a tremendous effort. I remember watching basketball games when I was a kid, and actually liking it when my favorite team was down by a large margin. The way I saw it, the deficit was just potential for a big comeback - maybe an unprecedented comeback, a game people would talk about for decades. While I knew that I might be witnessing a blowout, I also knew that I might be watching sports history in the making. I also knew that I wouldn't be anywhere near as excited if my team won by a large margin - it would just be too easy that way.

When you get frustrated at your lack of success with the opposite sex, stop for a moment and recognize that the same principle applies in your dating life.  If finding a boyfriend or husband were easy, you wouldn't care much for your relationships. Every man would be replaceable, just as you would be to every man. The more you improve yourself in order to find love, or the more years you spend maturing before you can recognize it, the more unique your story will be, and the more you will value the man who marks its end.


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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.

Why Rejection Is A Good Thing

If you get dumped by a guy you like, remember that although this is probably due in part to men playing below their league, it is also the product of you being ambitious in your relationships: you are trying to get the best guy you can, and therefore you are dating guys that might dump you. In moderation, this ambition is a good thing. If you were constantly settling for guys of a low caliber, then of course you would have more success, but you wouldn't be content. 

While it is certainly worthwhile to consider whether or not your standards are realistic, you should also acknowledge how lazy or apathetic you would be to settle for someone below your potential. If you aren't getting dumped by guys, you could probably be doing better.

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If you liked this post, you'll definitely like my book, Beyond the Breakup, which says a lot more about the importance of rejection and how to use it to grow into the kind of girl guys really want to commit to.

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