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Episode #307

Should You Date Nate: A Behind-The-Scenes Look At One of The Most Bizarre Dating Profiles Ever with Nate Rifkin

Recently, copywriter Nate Rifkin wrote a sales letter offering himself as a date to women. He built an entire marketing campaign called Should You Date Nate. What happened next was beyond belief.

Here’s a glance at what you’ll learn from Nate in this episode:

In one of the most unusual I Love Marketing podcasts ever, you’ll discover…

  • Why a “self-confessed greedy capitalist pig” wrote what E! News called “The Most Bizarre Dating Profile Ever”
  • How Nate spent a little over $800 on Facebook to promote his dating profile and made it go VIRAL  
  • THOUSANDS of Hate Mail Messages: Nate reveals how his “weird” dating profile got 250,000 visits over 7 days (He got a TON of hate and backlash, BUT also HUNDREDS of potential dates)  
  • Two MASSIVE mistakes Nate made in his dating profile (Nate shares what he would do differently if he could turn back time…)  
  • Planning For An Uproar: Real world advice for dealing with criticism, public attacks and hate mail


  • Nate has had a lot of success as a copywriter but not a lot of success in the dating world.
  • Gary Halbert put up a full page ad in the New York Times where he was selling himself as a date, Nate decided to do something similar for the modern age.
  • Creating chemistry is not the same as transactional selling.
  • Nate started out his dating sales letter unconventionally by starting with his “flaws”.
  • Make it easy for your customer by telling them exactly what to say when they call in.
  • You can use marketing for anything.
  • Nate began driving traffic to his sales letter with Facebook ads using a unique trick to make sure it was compliant with Facebook’s terms.
  • By targeting media organizations with his ad, he was able to get a lot of mainstream media traction which helped the ad go viral.
  • Even as a public figure, the negative feedback caused a lot of stress. Nate made the choice to unplug and experience the real world.
  • If you’re dealing with bullying on the internet, get out into the real world and connect with a real human.
  • People complaining about the the ad itself was part of the goal but making someone feel bad was not. Sometimes it’s better to just say “send photos.”
  • There is good and bad inflammatory.
  • The response was mostly negative but it resulted in over a hundred positive responses from women looking to go on a date. Nate had more dates than he could handle.
  • The political affiliation of the women ran the gamut, they weren’t exactly like Nate but found his profile interesting anyway.
  • Nate’s exit strategy shut off the flow of traffic by telling people directly it was a PR stunt.
  • He had to learn how to cope with all the negative feedback because it drove Nate to become paranoid and overly anxious.
  • Opening yourself up makes you vulnerable but it’s also very inspiring to people who want to see the real you. Humans want to connect.
  • Good marketing is not just the most effective way to make money, it’s the most effective way to save time.
  • Putting a closer spotlight on the positive qualities of what you want could be a better approach to finding what you want.
  • Putting yourself out there is like holding up a big mirror and shows you what people really think about you.
  • When you’re writing to a market that isn’t you, be very careful with what words you use. There might be just one line that breaks the rapport and it can happen in any market.
  • Nate started out by reading the Gary Halbert letters to learn copywriting but the trick is to just dive in and start testing their stuff if they want to get better.
  • If you’re not where you want to be, take action now.

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