Video: One Woman, One Year, One Hundred and Fifty Dates

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updated 1/23/2006 12:13:10 PM ET 2006-01-23T17:13:10
STORY

In 1998, Maria Headley, decided that her dating standards were just a little too high and for a year, decided to yes to anyone and everyone who asked her out.  She accepted the invitations without regard to sex, race, age, income or ethic origin. 

A hundred and fifty dates later, she met and eventually married Pulitzer Prize-winning playwright Robert Schenkkan, a man 25 years her senior, with two teenage children from a previous marriage.  It was perhaps a match she might not have considered if not for this experiment and the resulting open-minded that led her to date everyone from a homeless man to millionaires and everything in between.

Headly, who also wrote the book, “The Year of the Yes,” joined Keith Olbermann on “Countdown’ to talk about how she managed to take the dating world by storm.

To read an excerpt from their conversation, continue to the text below. To watch the video, click on the "Launch" button to the right.

KEITH OLBERMANN, HOST, ‘COUNTDOWN’:  I heard a description of the average date in an advertisement on the radio today.  And it was this:  You might as well just punch yourself in a sensitive part of your body and throw away $50 bucks.

And I can understand that description if it was somebody my age, but it sounded like it was a kid of about 20 speaking.  That was your age when you hit the “I'm sick of all this” wall.  What was the last straw? 

MARIA HEADLEY, WENT ON OVER 150 DATES IN ONE YEAR:  The last straw was a guy who called me up and said, “I'm listening to NPR.  Do you want to come over and make out?” 

And that just wasn't an aphrodisiac quality there for me.  I thought, “I'm dating the wrong kind of guy.”  And I thought I was getting so many offers elsewhere, just walking down the street in New York—there are eight million—you know, I thought there must be something different out there. 

OLBERMANN:  So with that, another use for NPR being decided against, you decide to say yes to everyone, and some of the everyones included a homeless person, non-English speakers, and other women.  That doesn't sound necessarily practical or safe.  Did you see it in those terms? 

HEADLEY:  Well, practical is something that, when you're 20 years old, it doesn't matter that much, practicality.  And safe, I was definitely not saying yes to people who were staggering drunk, or definitely on drugs, or married, if I knew they were married.  So I was trying to watch out for my safety.  I didn't give people my phone number or tell them where I lived or anything like that. 

OLBERMANN:  Where did the—not to make fun of his situation, but where does a homeless man take a woman out on a date to? 

HEADLEY:  I actually took him out.  I took him out for a falafel.  We just went for, you know, $5 worth of pita bread. 

OLBERMANN: Were there rules besides those fundamental ones of, as you mentioned, the drug and marriage thing?  Were there any other rules in that could have allowed you to say no? 

HEADLEY:  No, actually, not really.  I mean, I couldn't say yes to people who were underage.  Some underage kids hit on me, some 14 years olds.  I said no to them.

OLBERMANN:  Yes, you can't do that unless you're a school teacher.  So during this time you met your husband.  How did that happen?  That wasn't part of the project, was it? 

HEADLEY:  No, I wasn't actually look for a husband.  I was looking to fall in love.  And I met him at the Kennedy Center, and he was married at the time.  He was lots older than me, as you mentioned, kids.  All of these things were things that I thought, “Oh, no, no, no.” 

But he was a writing idol of mine, and I thought he was an amazing person.  I wanted to find someone just like him without all the baggage.  And then, eight months later, he called.  And he was getting divorced, and I had gone through 150 dates.  And my feelings had changed about what constituted a good man. 

OLBERMANN:  So did the whole experience, did they always say your standards are too high, standards—did it lower your standards or did it, as the other cliche goes, broaden your standards? 

HEADLEY:  It opened my mind, I guess, is what it did. 

OLBERMANN:  Ah, OK.

HEADLEY:  It made me much more willing to look at different parts of people that I wouldn't have noticed, because I didn't like the color of their shirt before, you know what I mean? 

OLBERMANN:  Yes.  Yep, no, I know that very well. 

HEADLEY:  Yes.

OLBERMANN:  A hundred and fifty dates.  There's got to be a best and a worst.  Can you summarize the two?

HEADLEY:  The best date that's not my husband was a date with a subway conductor who took me to Coney Island.  And we went swimming.  And it was the end of October, so it was freezing.  But it was something I would never have done, and it was so much fun.

And the worst one—there were several bad ones—but the worst one was this guy who  gave me an address to meet him at and it was a strip club.  And he left me for a lap dance. 

OLBERMANN:  By the way, I only know 11 men who that could be, so I really can't help you out on that one.  And I wouldn't divulge it anyway.

HEADLEY:  Yes.

OLBERMANN:  But this last question, would you recommend anybody else, male or female, try this? 

HEADLEY:  Yes.  I think everybody could stand to have their mind opened a little bit.  Everybody's probably too critical.  I think that this is something that could definitely get you out of a rut. 

Watch 'Countdown' each weeknight at 8 p.m. ET

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