Bezos and Gates give their best tips!

As a Weekly World News reporter, I’m used to having access to practically everything. Classified government documents? Name a country. Alien autopsy reports? Pick a species. Breakfast with Bigfoot? Did that last week (he had the French Toast and it was excellent).

Recently I was offered a special kind of access that made even this veteran newsie giddy with excitement. For the first time in…ever…two of the world’s wealthiest humans, Bill Gates and Jeff Bezos, are single and hitting the dating scene. Together.

After getting wind of this Billionaire Boys Night Out, I did a little sleuthing and uncovered their itinerary. I shadowed them at a respectable distance for the entire evening (completely unobserved by the two men) and took notes on what I saw.

With 54 years of marriage between them, I expected they’d be a little rusty. But with a combined wealth of more than $573 gazillion, I also thought they would’ve hired a consultant or something. At the very least some writers? Because Bill and Jeff’s pick-up lines didn’t do much to break the ice. Quite the opposite, in fact. They sent nearly all possibility of having a meaningful conversation into a glacial deep freeze.

At first, Bill and Jeff seemed to operate from a single playbook, each trying the same or similar lines to get an initial “read” on the room.

Here is a sampling of the lines both men tried with varying degrees of success:

  • Can I buy you a drink? Or maybe a private island?

Best reply I heard all night? “Sure. I’ll have a Grey Goose Martini, up. And a secluded coral atoll in the Caribbean. Please.”

  • Man there are a lot of zeroes in this bar—almost as many as after the “1” in my bank account.

In general, math references are not your strongest lead. But in this case, it was actually quite effective.

  • I’d give a million bucks to see that smile again. No, really. Hit me up on Venmo.

All in all, Jeff and Bill coughed up at least $15 million that night before retiring this approach.

After getting more stunned silence than phone numbers, Bill and Jeff decided to try a more personalized approach. Something unique to each man.

Here are some of Bill’s best, if you can call them thaT

  • They call me Windows 10. And I’m here to crash your laptop.

Not effective and a little creepy. This caused more than one restart on Bill’s part.

  • Is your name Bing? Because you got what I’m searching for.

Much like Bing, this line was not well received.

While Gates was definitely showing some rust, Bezos seemed a bit more polished. Here are a couple of Jeff’s gems…

  • My last divorce settlement was bigger than the GDP of most countries.

Ok, normally I would say mentioning past relationships is a bad idea. But…

  • Are you one of my subscribers? Because you are looking PRIME!!

This could’ve been a winner. But every time Bezos met an actual non-subscriber, he spent 20 minutes trying to convince them to join Amazon Prime.


After a few hours with no luck, Bill and Jeff finally gave up and left. Both men, of course, made exits worthy of their billionaire status. Gates called his private helicopter, while Bezos paid three random dudes from the bar $20k each to carry him on their shoulders and chant “AMAZON! AMAZON! AMAZON!” the whole way home.

It’s easy to see why neither man made a love connection that night. But I will say this: at least they had the courage to put themselves out there. Easier, I’m guessing, with a few billion in the bank.

If there is one thing this evening verified for me, it’s that having a lot of money (most of it, even) doesn’t make it any easier to meet people. Neither do pick-up lines, for that matter.

The only way to make true and genuine connections is to simply be yourself. Whoever is drawn to you in those moments is someone worth talking to. Just don’t open with a cheesy pick-up line. Trust your boy Flip on that one.

Until next time, loyal readers. Flip. Out.

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