There are three reasons why you can’t make the leap from date to relationship

“If you want to date an emotionally functional human adult, then you need to be an emotionally functional human adult.”
“If you want to date an emotionally functional human adult, then you need to be an emotionally functional human adult.”
Image: Reuters/Francois Lenoir
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Nobody wins on Valentine’s Day. The holiday puts everyone in an awkward situation.

If you’re not seeing anybody, then it’s an incessant and unnecessary reminder of your solitude. If you are seeing someone, but aren’t serious yet, then you have this awkward “Should I say something? Should I not?” situation where you’re afraid that no matter what you do, it’ll give the wrong impression. And if you are in a relationship, then there’s all sorts of heightened expectations for chocolate and dinners and candles and violins and puppies and other crap, all of which will at best come across as forced and at worst be entirely disingenuous.

With that said, amidst the seas of flowers and ponies, I do make a point to write some dating advice on Valentine’s Day each year. It’s usually pretty brutal dating advice as well. Call it my little tradition.

So let’s keep the streak alive. This year I’m going to cut to the chase: Here’s why people who are perpetually single are perpetually single.

1. You don’t respect yourself

The respect and admiration you receive from others is proportional to the respect you receive from yourself. If you take care of yourself mentally, emotionally, and physically, then others will be attracted to the prospect of taking care of you mentally, emotionally, and yes, physically.

Don’t believe me?

Try it for a month. Take care of yourself. Exercise and eat well. Sleep well at night. Work hard and plan ahead. Be social. Eliminate bad habits. Speak about your ideas without inhibition and expect nothing in return. Share things based on the simple pleasure of sharing. Pursue others out of earnestness and not out of obligation or desperation. Don’t accept judgments made by yourself or others. Don’t take rejection personally. Rather than see the world in terms of ranking and competition, choose to see the world in terms of compatibility and incompatibility. Then take it on as your job to find the compatibility.

Try it for a month and see what happens.

I realize it’s not easy. But that’s kind of the point. Being an emotionally functional human adult is actually a difficult endeavor. But if you want to date an emotionally functional human adult, then you need to be an emotionally functional human adult. It’s a radical idea, I know.

2. You have absurd expectations

There are two new dating stereotypes that have cropped up this generation. They are:

  1. The man who is fat, balding, underemployed, anti-social, and unhygienic who decorates his apartment with his collection of original, mint-condition, Star Wars action figures (all in fighting poses), who spends his weekends engrossed in comic books and internet porn, and who is then perpetually frustrated that every woman he likes is somehow unable to appreciate all of his amazing qualities. He then comes to the conclusion that—obviously—there’s something horribly wrong with the women of the world.
  2. The fashionable, beautiful, 30-something, career woman who wants to settle down, but despite having dates lined up every night of the week, she laments that there are “no good men out there.” The last man she dated was an accountant, played racquetball, and spoke French. But she dumped him because he had bad fingernails and didn’t want to go to business school. The man before that won the Nobel Prize in chemistry, but she dumped him because chemistry is such an impractical profession anyway—I mean, really, get a clue!

The man feels entitled to date anyone despite the fact that he brings basically nothing to the table in an intimate/sexual relationship. The woman brings something to the table, but feels entitled to date someone who brings everything to the table in an intimate/sexual relationship. Both are terribly delusional in regards to their dating expectations.

These flavors of delusional expectations come down to perfection—people who expect perfection in others and people who expect others to acknowledge the perfection in themselves. It’s debatable which is more insufferable.

There are people who assume that any sort of disagreement or argument signals a deathly incompatibility and a future of pure misery, so they end it. Then there are people who expect the opposite sex to fall down and beg for their attention and affection and then get genuinely pissed off and vicious when they don’t. There are people who think that because you shared a chicken basket and watched a Tom Hanks movie together, you’re now owed a phone call every single day and if that phone call doesn’t come they go on a screaming tirade.

It’s really simple: We all have our own imperfections. Everyone we date also has their own imperfections. Intimacy and romance is determined by people who have comparable and complementary imperfections to one another.

Learn to appreciate some people’s imperfections. Learn to appreciate and improve upon your own. Otherwise you’re going to be single (and angry) for a very long time.

3. You haven’t developed the skills for intimacy

A lot of people are great “on paper” daters. What I mean by that is that they go on dates regularly. They’re attractive, attentive, have good jobs, interesting skills, and hobbies. They do the dinner conversations, they laugh in the right places, they talk about their lives, their families, their careers, their aspirations, their dog’s strange bathroom habits. They nail everything and yet…

…nobody sticks around.

Eventually, the phone stops ringing, the lame excuses pop up, or the ubiquitous, “We should just be friends” comes out.

Ultimately dating and finding a partner is an emotional process. People like this get the surface-level behaviors right, but they never engage the depth of their emotions and connect where it matters. It’s like the difference between composing a concerto on piano and simply performing somebody else’s concerto.

Generating intimacy in a relationship requires emotional investment and vulnerability. That means you need to open up about yourself in ways that may not be completely comfortable. It means exposing yourself. It requires you to share opinions and values that may polarize people and generate rejections. It requires you to be bold and take risks in going after what you want.

To generate emotional intimacy with others, one must open up and discover the emotions within oneself. Sexual are romantic relationships are often objectified—they’re treated as boxes on a checklist or entries on a resume. But intimacy is something that happens organically through the mutual expression of emotions and values. It’s a box that can’t be checked. It’s a resume that can’t be filled in. It’s unconscious and personal and unnameable. And one cannot generate that deep intimacy if one is not open to those deep emotions and values within oneself.

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