The Millionaires

Dylan talks about succumbing to peer pressure, making a move on Arielle, and more!

Apr 6, 2010

 

When approached about going on Millionaire Matchmaker, I did what I always do when faced with a difficult decision. I assessed the situation and ran a cost/benefit analysis.

Pros: A unique experience. Introduce my company (Box.net) to a new audience. Showcase boyish charm and rugged good looks. Potentially I’ll sharpen my dating skills.

Cons: Experience couldn’t be more out of my comfort zone. Expose a multitude of flaws to a new audience. I’m terrified of Patti. Potentially I’ll be disowned by my family.

Ultimately I threw out my analysis and succumbed to peer pressure. I began to doubt this decision as my LA trip approached, but once I arrived everything moved so quickly that I didn’t have time to worry. The show was surprisingly real – I wasn’t given advice, lines, or makeup – I just showed up and the cameras started rolling. Within thirty minutes Patti had labeled me a geek and instructed me to “dance sexy” with a stranger in moose-themed pajama pants. (To be fair, the wardrobe selection was my own doing). The lesson was awkward, but if the goal was to force me to loosen up and not worry about looking cool, it totally worked.

Then came the mixer. I secretly hoped that the other millionaire would be seventy and creepy so that I’d look good by comparison, but Hillel was a far better partner in crime – it was impossible not to have fun around him. Initially, the conversations felt forced and repetitive, but Patti’s team came to the rescue – they kept things moving and I didn’t even notice Arielle until they pushed her in front of me.