Her year of boldly flirting with and accepting invitations from everyone who showed her a spark of interest (women and the homeless included) landed her 150 dates, a husband and a slew of stories for her memoir, "The Year of Yes."
According to her Q&A portion of theyearofyes.com, a wide-open dating strategy can increase your chances of finding love.
Imagine smiling brightly at the person in front of you in line at Wendy's as his skull-tattooed hand thrusts money over the counter for three orders of chili.
Then imagine saying "yes" when he asks for your phone number, and later for a date. And I'm not talking about the occasional skull-tattooed Wendy's patron who happens to be sort of hot. I'm talking about going out on such limbs constantly, leaving your comfort zone of dating prospects for a full year.
I think people can trust their instincts about who they are attracted to without testing the extremes. A man I'll call Grill Guy comes to mind (he was named such because he worked the grill at a yucky seafood restaurant where I served during college).
Grill Guy was all wrong for me, if I abided by the superficial disqualifying traits he possessed. He never spoke of plans to explore other career options. I'm not sure what his hair looked like because of his everpresent Green Bay Packers cap.
Maybe I'm snobby. He just wasn't a person I'd consider dateworthy.
But he was hilarious and had the most beautiful teeth I'd ever seen. He was the only bright spot at a terrible job.
So as we munched our umpteenth plate of rock shrimp out back by the ice machine, and he asked me what I was doing after work, I ignored my impulse to lie about needing to study.
Who was I to hold this nice guy's financial status against him? I agreed to meet him later. I just said yes, Ms. Headley.
And we had big fun when we hung out, chatting it up long after the restaurant was closed and sneaking in for night swimming at the DeLand Holiday Inn pool.
But then one day a woman came in to pick up some to-go food, and Grill Guy went out to the hostess stand to talk to her. He gave her a quick kiss, and the woman, and the diamond she had on her left hand, were gone. That summer, the two were married.
Dating without selectivity makes for an interesting memoir, but trusting your instincts about new people seems to be a better strategy. If someone initially turns you off, maybe that's for the best.
Why accept 150 dates to give you 150 second chances to reaffirm your first impression?