Take it down a notch or ten, Nate
There's no sugar-coating it: Dating is tough. You can put yourself out there openly, honestly, and confidently in hopes of meeting your soulmate, but there's no guarantee that the universe will reciprocate your efforts. Still, there is a limit to just how direct you should be when you're first trying to meet that perfect partner, and our friend Nate here seems to have found that threshold.
Nate is an accomplished man, you see, but not a terribly nuanced one. Rather than, say, leaving some of himself to the imagination, Nate decided to create a personal website—the aptly-named shouldyoudatenate.com—to help him in his quest to find the love of his life. The website is a feature-length résumé on his professional accomplishments, personal goals, preferences in a partner, you name it. For examples, he's a libertarian and a hard-working entrepreneur; he loves meditating; he considers himself an outsider; and he's 6'4", as he so proudly boasts at the top of the page.
Most important, though, he's offering a free, three-day vacation to the interested woman who sends him a message and strikes his fancy. Ladies, if this manifesto didn't leave you completely weirded out by its conclusion, then you may simply win the prize by default. Needless to say, Nate's attempt at attracting "the One" comes off as, well, a little much. This is certainly one way to earn the attention of the opposite sex, but it doesn't strike us as the most effective method.
But, hey, as Nate himself says, "If you go through your whole life being comfortable, you're doing it wrong." Which is true enough, but we'll also point out that being uncomfortable doesn't necessarily mean you're doing it right.