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The Complete Guide to Fix Your Dating Failures

Fix Your Dating FailuresI’m sure I’m not shocking anyone when I say that dating can be frustrating.

“The hell you say…”

One of the hardest parts of dating is that, more often than not, you’re doing it in a vacuum. It’s not exactly as though you can hand out comment cards to your dates and ex-girlfriends and get some constructive criticism. First, it’s not their job to fix you. Second, many times it’s not going to be actionable advice anyway. And third, let’s be honest: they just left you for a reason. What exactly do you think they’re going to say?

Points for creativity, though...

Points for creativity, though…

Unless you’ve got someone who’s actually watching every move you make, you’re going to have to do your own relationship troubleshooting. So from constant strings of rejection, to flakes to bad break-ups, here’s how you learn to fix your dating mistakes.

Write Down Everything

One of the first things you should be doing if you’re having a lot of dating problems is to start keeping records.

No. Seriously.

Part of the reason why dating issues are often so hard to solve is because you’re too close to the source. It’s a forest for the trees issue; you’re so up close and personal that you can’t see what’s going on. You’re frustrated, you’re horny, you really really want to make that next date work… you’re not really in any position to be at all objective or to take the larger view. If you want to start pinpointing issues, you need to have the raw, dispassionate data and you’re not going to have that just from your day to day observations. This is where journaling comes in.

...maybe not like this, though.

…maybe not like this, though.

The benefit of keeping a journal is that it is a record of events that’s going to be more reliable than just trusting your memory to keep everything straight. It’s a concrete documentation of your emotional state, of your behavior, your immediate thoughts and reactions. In a lot of ways, it’s a method of having a long-form conversation with yourself. And – more to the point for this exercise – keeping a dating journal means that you’ll have data and perspective.

Here’s how it works: you want to keep track of everything about your issue. Personally, I’d suggest designating a specific journal or file exclusively for this purpose; this makes it much easier to look at it en masse when it’s time to go back over what you’ve written. If you already have a journal of some form, then make sure that any entries that involve your dating problems are tagged appropriately so you can find and group them quickly and efficiently. Each day, keep a record of what you’ve been doing with an eye towards your particular problem. If you’ve been making cold approaches, then track everything about each interaction: where you were, what you wore, how you felt, what you said, what you did physically, how she responded, how long you were in the conversation, at what point it ended, etc. If you’re dealing with relationships falling apart regularly, then write about the two of you together. Again: try to write down as much as you can, as dispassionately as you can. I realize it’s difficult, but try to keep emotional judgements or editorials to a minimum and strictly adhere to the facts: who said what, who did what, etc.

Then, at the end of each month, stop and review everything you’ve written – start to finish. The point of this monthly review is to look for patterns. Are your approaches ending in the same place every time? Are people continually starting to edge away or making excuses to leave? If you’re dealing with relationship problems, are your fights about the same issues every time? Are you constantly finding that you’re drained after talking to them? This is how you start to narrow in on where you’re having problems and correcting them.

Get Out Of Your (Dating) Comfort Zone

Another issue that comes up when you’re having problems dating: you’re too comfortable.

I’m always saying that dating is a skill and the conventional wisdom is that it takes 10,000 hours to master a skill1. The issue that comes up very quickly is that mastering a skill isn’t about simple repetition. Doing, say, a thousand cold approaches, isn’t going to make you a master pick-up artist, any more than singing “‘enry the ‘eighth” over and over again is going to get you a recording contract and a Grammy.

It is, however, a great way to get people to leave you alone.

It is, however, a great way to get people to leave you alone.

The point is that it has to be deliberate practice. A musician doesn’t just play the same song over and over again, they play scales, they play the song faster, slower, in a different key. Someone trying to get better at basketball doesn’t just do free-throws and call it a day; they run drills, they work on making shots from different parts of the court, they keep track of whether they’re missing by falling short or overshooting the basket.

If you’re doing the same thing over and over and over again and getting absolutely nowhere, then you need to shake things up. Odds are good that you’re not taking risks and are going for what you know is “safe”, despite the disappointing results. You need to do things that get you outside of your comfort zone and push your limits… especially if it’s in areas where you’re weak. Back when I was mostly doing bars and clubs, approaching groups was terrifying for me at first. I thought it was going to be like running a gauntlet of judgement and intimidation – doubly so, if it was a mixed group of men and women.

…yeah a lot like that, actually.

But learning how to handle groups of people was a key part of learning how to navigate social circles as well as trying to pick up women… and that meant I needed to work on it. So I had to push myself beyond where I was comfortable and shore up a skill where I was especially weak. In this case, I had to make a point of specifically approaching groups until I learned to be more comfortable engaging with folks. That helped me improve overall – not just with dating but socially in general.

And while we’re talking about deliberate practice…

Do Some A/B Testing

While you’re narrowing in on where your sticking points lie, you’ll want to start experimenting with some changes to see what works and what doesn’t work. You might try your standard approach with one group, then try something slightly different with another. In corporate-speak, this is often known as A/B testing; where you present one version to one group and another version to a different group in order to see which evokes the better response.

And in this moment I witnessed the birth of corporate-strategy-as-dating-strategy and wept for the abomination I'd created...

And in this moment I witnessed the birth of corporate-strategy-as-dating-strategy and wept for the abomination I’d created…

The place where this is easiest to implement is when it comes to online dating; you can make tweaks to your profile and see how much it does or doesn’t affect your response rate. Major changes like different photos are more likely to have larger, more noticeable results (presuming that you, y’know, use good photos) but changing parts of your profile also can keep the attention of the people your photos bring in. Similarly, adjusting your initial email can bring different results.

In person, you’ll want to consider changing up some of the variables as well. If you notice in those records I told you to keep that you lose people’s attention soon after introducing yourself to them, then you should experiment with what you talk to people about or how you approach them. You might change your style slightly and see if that helps change people’s responses as well – another area where getting out of your comfort zone can be surprisingly beneficial.

In fact, most of A/B testing when it comes to dating is about pushing yourself out of your comfort zone and trying new things. Much of it involves giving yourself permission to fail; yes, any one thing you try won’t likely be the magic bullet that turns everything around, but what you learn from it is more important. The things that don’t work help lead you to the things that do.

Meanwhile, there’s something else you need to consider…

Make Sure You’re Pursuing the Right People

One common sticking point I see often are the times when folks are chasing partners who’re just wrong for them. The fact that you may have a “type” doesn’t mean that you’re compatible with them. Just because you’re attracted to somebody doesn’t mean that the two of you would work – even in the short term. In the end, it doesn’t matter whether your patter’s on point and your charm is killing it; some people just aren’t going to click, no matter how much you may want it.

"That's nice. Bye!"

“That’s nice. Bye!”

If you have a type that never seems to like you back, it’s worth examining just what it is you like about them in the first place. Many times, people will pursue a particular type, not because they’re compatible but because of what that person represents. Part of the appeal of the Manic Pixie Dream Girl – in fiction and in life – is that she fills a void in people’s lives. She’s free in ways that they wish they were and drags them into that same quirky, care-free life. Except in reality, they would never work; if they could be that care free, they already would be. The problem is that these men feel dissatisfied with their lives and want someone else to fix it for them.

Remember: opposites only attract in magnets, not in dating. No relationship is going to magically transform you into a different person.

One common variation of this problem is when a person’s archetype and lifestyle is diametrically opposed to the people they’re hoping to attract. I see this all time in online dating: their profiles are catnip for a very specific type of person… who happens to be the antithesis of who they’re hoping for. Having photos of you and your adorable baby nephew or niece is going to appeal to someone who’s looking to settle down or wants a family soon… not to the young party girl who wants a NSA fuck-buddy. Similarly, your brotastic abs-out-for-the-ladies, look-at-us-partying-woo profile isn’t going to appeal to hippie chicks or more introverted artsy girls with walls of polaroids. Rough-and-tumble bikers may hook up with sexy doctors on TV, less so in real life.

Bring Something To The Table

OK, this one’s not a quick fix. But it’s an important one: if you want any dating success, you have to bring something to the table. And no, an absence of glaring flaws is not the same thing as bringing something to the table. To put it another way: do you pass the Grimes test?

This is Grimes.

He's also conveniently not owned by a particularly litigious gaming company..

He’s also conveniently not owned by a particularly litigious gaming company..

Grimes is a kaiju, born out of unholy alien science and toxic waste. He’s not bad looking as kaiju go, has a generally cheery disposition, a decent job and a place of his own but no real interests or hobbies. He’s never hit a woman, never sent unsolicited photos of his genitals (in as much as he has any), never creeped on a woman, stalked through her social media profile or pursued someone who wasn’t into him. He’s never harassed a woman, sent threatening or sexually explicit messages or violated her boundaries.

So what do you have going for you that Grimes doesn’t2 that would make you appealing to women? Are you better than Grimes or not?

If the best you can say about yourself is “I’m not a douchebag”, then you’re not going to appeal to anyone. You don’t get extra credit for meeting minimum standards. It’s like a car celebrating that it has seat-belts as though it were a major accomplishment instead of something that every car comes with. If you want to be appealing to women, then you need to have things that you do that make you interesting. Just being “nice” isn’t enough. To quote Glenngary Glenross: “Nice guy? I don’t give a shit. Good father? Fuck you, go home and play with your kids. You want to work here, close.” Want sex? Want a relationship? You have to bring something to the table.

Some people bring looks to the table and for some folks, that’s enough. Other people are funny and can make people laugh. Other folks are talented singers or musicians or painters. Still others lead interesting lives full of travel or excitement. If you don’t have something to make you appealing, then you’re not going to appeal to folks. The fact that other people have things that they bring to the table that you don’t doesn’t matter. They’re not you and you’re not going get better trying to be them. Don’t worry about what other people are doing, worry about what you’re doing to be more interesting and attractive.

There’s no one thing that’s going to be the universal attractant; you need to find your thing. Invest in yourself, in your lifestyle and in your passions. Find those parts of you that help you pass the Grimes test.

And when you do, you’ll find how those dating failures start to disappear.

Fix Your Dating Failures

  1. There’re a lot of questions around this bit of received wisdom, but it makes a convenient rule of thumb for our purposes
  2. And no, “not being made of toxic waste” doesn’t count. See that bit about “meeting minimum standards” and quit trying to be clever.

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