David DeAngelo and Double Your Dating

4 min read

If you were a young man online in the early 2000s, there's a fair chance an email from David DeAngelo landed in your inbox. He wasn't the flashiest name in pickup. He didn't host a TV show or star in a bestselling memoir. But two of his phrases, "cocky and funny" and "attraction isn't a choice," became some of the most repeated lines in dating advice, and you'll still hear them today.

Who he is

David DeAngelo is a pen name. The man behind it is Eben Pagan, an American entrepreneur. According to an archived Wikipedia article on DeAngelo, Pagan started out as a student of Ross Jeffries, and his ideas first circulated through Cliff's List, an online seduction newsletter of the time. His commercial career began in 2001 with an e-book called Double Your Dating.

The e-book grew into a company of the same name that sold dating advice for men, mostly over the internet. Later titles included Advanced Dating, 77 Laws of Success With Women and Dating, and Deep Inner Game. The business leaned heavily on his email newsletter, which helps explain how far his ideas spread.

Pagan later moved into teaching business and marketing under his own name.

If you want the earlier context, Ross Jeffries and Speed Seduction covers where DeAngelo started.

The two big ideas

Attraction isn't a choice

DeAngelo's central claim was that you can't talk someone into being attracted to you through flattery, gifts, or being agreeable. As the archived Wikipedia article summarizes it, he argued that attraction happens automatically when someone perceives qualities like confidence, lightheartedness, humor, and independence.

There's something useful in that. Lots of shy, decent men assume the way to win someone over is to be endlessly accommodating: buy the drinks, agree with everything, compliment constantly, hope it adds up. DeAngelo's point was that it usually doesn't. People are drawn to someone who has a life, opinions, and a sense of humor, not someone auditioning for approval.

Where it goes wrong is the word "automatically." It encourages you to think of attraction as a switch you can flip with the right behavior. It isn't. Someone can find you funny and confident and still not be interested, for reasons that have nothing to do with you. Taking that seriously is the difference between confidence and entitlement.

Cocky and funny

"Cocky and funny" was DeAngelo's best-known technique: humor built on playful mock arrogance, meant to show you're relaxed and not desperate for approval. The archived article notes that DeAngelo himself warned about balance. Too cocky comes across as insecure, and all comedy comes across as goofy.

An honest version looks like this. She says she's terrible at pool. You say, "Good, then I might actually win one tonight." That's light, self-aware, and about the situation.

The version that goes wrong is teasing that targets her. Commenting on her looks, her clothes, or her intelligence "as a joke" is a neg with a nicer name, and Flow doesn't recommend it. If the laugh comes at someone's expense, they'll feel it, even if they smile. More in negging: what it is and why it backfires.

Critics also pointed out that the style can come across as insecure and phony when it isn't natural to you. If sarcasm isn't your humor, forcing it will make you look like you're performing.

Other DeAngelo ideas

A few more concepts from his material circulated widely:

Why it caught on

DeAngelo's material was plain-spoken compared with Jeffries' NLP jargon, and it promised something simple: stop being needy, be confident, be funny. Delivered by email, it could reach people who'd never go near a seduction forum, and it told them dating skills could be learned.

What "not agreeable" looks like in practice

The trap DeAngelo described is real, so it's worth making the honest version concrete. Here are a few common moments and two ways to handle each.

She says a movie you love is overrated. The approval-seeking reply is "Yeah, I guess it is." The honest one is "No way. Okay, what didn't you like about it?" You're disagreeing, but with curiosity, and now you're having an actual conversation.

You're asked where you want to go. "I don't mind, wherever you want" feels polite but puts all the work on her. "There's a taco place two blocks over I've been meaning to try. Up for it?" is a suggestion she can still say no to.

You like her. Hiding it to seem cool is its own kind of game. Saying "I'm really enjoying talking to you" is direct, and it doesn't ask her to do anything with it.

None of this is cocky. You're having a point of view and sharing it kindly.

What to keep, what to drop

Keep: you can't earn attraction by being agreeable. Have your own life and opinions. Use humor. Don't apologize for being interested.

Drop: treating attraction as a switch, teasing aimed at someone's insecurities, and holding back warmth as a strategy.

The honest replacement for "cocky and funny" is simply relaxed and funny. Say what you think, laugh at yourself, and pay attention to whether the other person is enjoying the conversation. If you want to work on how you come across, body language that reads as confident is a practical next step, and famous pickup artists puts DeAngelo next to the other big names.

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