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How Tim Ferriss Hacked His Dating Life

Tim Ferriss is a leading expert in accelerated learning. He mastered the art of language acquisition, lost twenty pounds of body fat in thirty days, and conquered earning a six-figure income by working merely four hours a week (would you expect less from the author of the 4-Hour Workweek?). Newsweek named him “the world’s best guinea pig” and the NY Times called him a “cross between Jack Welch and a Buddhist monk.”

In his latest TV show, The Tim Ferriss Experiment, Ferriss partners with the world’s best and most unorthodox teachers to attempt mastering everything from open-water swimming to Brazilian jiu-jitsu to professional poker.

As Ambiance Matchmaking is based in the San Francisco Bay Area, we have been anxiously awaiting for Tim to become a guinea pig in the dating world. So, we could hardly contain our glee when his episode, The Dating Game materialized in our inbox. Better yet, it wasn’t solely about online dating, Tim also immersed himself into the worlds of organic dating and professional matchmaking.

It was comforting to see someone like Tim, a smart, successful, charming, and handsome man, struggle as much as the rest of us. It was one of the hardest experiments he attempted, he admits, due to his emotional insecurities remnant from grade school. But, as Eleanor Roosevelt wisely said, you should do one thing every day that scares you, and that’s exactly what he did…

Approach #1: Online Dating

Result: High Quantity, Low Quality

Tim teamed up with Samy Kamkar, a computer programmer most notably known for spreading the biggest computer virus of all time through MySpace. But after getting raided by the United States Secret Service, he decided to pursue new projects. What better way to utilize your hacking skills than to help Tim Ferriss find the love of his life?

Kamkar created a number of programs to hack online dating. First, he downloaded every dating site profile to his computer, which created a database of all the single profiles in LA. Within this database, he could automate the repetitive task of searching profiles for certain characteristics. For example, he setup a program that automatically assessed the writing ability of each single and gave it a high school level grade. If you couldn’t write better than a 7th grader, for example, you were sent to the spam folder.

He used this kind of filtering system (called the Bayesian filter which determines what discarded profiles have in common in order to exclude similar profiles in the future) to filter through thousands of other profiles. This reductive approach provided him with 1,000 quality profiles out of the initial 20,000.

Obviously, not everyone has programming skills elicited by the NSA. So, when Tim asks how the average Joe can pull off this time-saving task, Kamkar suggests hiring a developer. “It could save yourself hundreds – maybe thousands – of dollars in dead-end dates,” he says.

Kamkar also used online services to decipher which of Tim’s photos would grab the most attention. For example, OKCupid’s My Best Face (which is now discontinued, but there’s a similar services called Photofeeler) helps find your best photo and the type of person most likely to be attracted to it. After receiving hundreds of responses, a shirtless Tim holding a kitten was the winner.

Approach #2: The Cold-Approach

Result: In-between

This was the most painful to watch, but most beneficial in terms of personal and social development (I would assume). With the help of Neil Strauss – seven-time New York Times best seller – Tim approached women at a San Fransisco farmer’s market. The goal was simple: approach a girl and ask her out.

At a first glance of Neil – a thin, nerdy chap – you might wonder why he was chosen as Tim’s dating muse. However, few people know that he was admitted into a secret society of pickup artists for a full two years while working as a journalist, which is chronicled in his book, The Game: Penetrating the Secret Society of Pickup Artists.


Neil Strauss’s 9 rules for Tim to follow –

  1. The Three Second Rule
    You have to approach a woman within three seconds or else one of two things will happen – you either creep her out, or you psych yourself out.
  2. Approach A Group
    It’s better to approach a group of women – they are less likely to have their guard up.
  3. Seem Spontaneous
    Your initial question must seem spontaneous, and not pre-conceived.
  4. Keep Weight On Your Back Foot
    When your body language shows you’re not staying very long, she won’t feel pressured or trapped into the conversation.
  5. Ask A Neutral Question
    Keep the initial question light and casual.
  6. Include Friends In The Conversation
    It’s the polite and sociable thing to do, and she will appreciate the added effort.
  7. The “Wait” Question
    Following your initial, neutral question, you will need an additional question to find common ground.
  8. The Hook Point
    Find a reason to ask for her number.
  9. Keep Talking
    Continue the conversation post-phone number to avoid “buyer’s remorse.”

Tim eventually approached “Annie” to ask the initial, neutral question. “I’m shopping for my sister and not sure her sweater size. Is it better to go bigger or smaller?”

This was followed by Tim’s “wait” question to find common ground. “I actually have to take her out to eat – are you a local here?” She responded, “Yes, I work for restaurants, actually,” which was exactly what Tim needed to spark an effortless dialogue on a topic he could dominate: San Francisco restaurants.

Finally, the hook point – “Do you have a card or something? Maybe I’ll swing by your restaurant,” was the perfect closer.

Approach #3: Professional Matchmaking

Result: Low Quantity, High Quality

Tim hired Silicon Valley’s fiddler on the roof to find his Natalie Portman doppelgänger. His deal-maker included someone with a high EQ and perfectly sized rib cage fit for tango dancing.

This method is essentially diametrically opposite of the cold-approach. When approaching women in real life, he had a visual read first. Now, his matchmaker will put a higher priority on intellectual and emotional compatibility, while keeping attractiveness on a fair scale.

A match is picked following a thorough uncovering of Tim’s makers and breakers pertaining to ethnicity, religion, lifestyle, family, and personality type, combined with an instinct for with whom she thinks Tim would have great in-person chemistry.

The Finale

Tim now has three women on his dating horizon gathered from his triad of hackers, matchmakers, and pickup artists. Rather than going on individual dates, like a normal person, Tim took a more bold, offbeat approach. He invited all three women to one cocktail party. If this idea sends your blood pressure through the roof, it actually ran pretty smoothly (albeit, he was three-deep when his dates arrived).

He was able to see how the women interacted with his friends and vice-versa. If he didn’t have chemistry with one of them, there were plenty of other cool gentlemen in the room. Not a bad idea, eh?

As Neil there as his guide, he instructed Tim not to “follow the attention” given to him by these women. Rather, he had to commit (at some point) to one woman, or else he would “burn out.”

So, which dating method yielded the best return? Well, he hasn’t said yet. “It completely depends on how much time and money you have to devote to finding your match,” he concludes.


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Taylor Wade

Taylor is one of the founders of Ambiance Matchmaking. She now dedicates her time to curating content for our community through her podcast and blog. Writing and podcasting is the art of great story-telling. As a relationship writer and editor, she has always sought to capture the reality of the dating experience, full of drama, friction, and joy. The best mind is an open mind, so she specializes in asking questions and approaching a story without preconceptions.

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