Cindy Steps out

She is Cindy Margolis. playboy cover girl. Author and fertility expert. Onetime "most down­loaded woman" and "queen of the Internet." Certified MILF.

She is 42, newly single and lookin' for love.

And she could be yours, at least for a night: Enter our contest for a chance to take Cindy on a date to the Playboy Mansion (see below). If you do happen to win, this guide could prove useful.

Until now she has never been single.

Not for long, anyway. We're talking a high school sweetheart, a long-term relation­ship and then her (freshly) ex-husband, for a total of three men in her whole life.

She cannot get a date. Her friends are no help. "I tell them to fix me up," she explains, "and everybody says, Oh please, you can get anyone you want.' Stop saying that! How can I get anyone I want? Tell me—how? I've been single for six months and haven't had one date."

She blew it with Matt LeBlanc. "He was my first date after that long-term rela­tionship," she says. "This was at the height of Friends, and women were throwing themselves at him. I thought I'd be differ­ent because I wouldn't sleep with him right away. Girls sabotage themselves to keep from doing things they know they might do. I thought, I'll wear granny panties; if I'm wearing granny panties, I won't sleep with him. We ended up taking a Jacuzzi, and he saw my granny panties, which I did not take off. He never asked me out again."

Today she owns more lingerie than Jesus (text concluded on page 119)

CINDY MARGOLIS

(iiinlinui'dJrom fxigi' 102) (or would, il Jesus owned lingerie) and not a single pair of granny panties. "The whole time I was married 1 never wore the same lingerie twice lor my husband." she says. Don't get the wrong idea; (his is not an Imelda Marcos situation. "I never pay for lingerie." she says, as if no one should ever have (o. "I'm not spending my kids' college money on bras and panties, i get it free at photo shoots. The next guy in my life— maybe the contest winner—has scored. I have the most outrageously sexy lingerie, and I haven't worn it for anyone yet." i She has solved the age-old paradox of lingerie. You know: Women love putting it on. men can't wail to rip i( oil. "I like to wear a bra but show my breasts," she says. "I like it open. 1 like them out, not covered at all. I'll wear garters and stock­ings but not panties. Or I'll wear crotch-less panties. I'll lei you see everything you want to see. For me. lingerie is just a pretly package. We can still do every­thing, and it doesn't have to be ripped oil me the second we're getting into it. When we're done I'll still look almost perfect, yet all the parts we needed were, you know, right there (o have fun with." (>. She regrets past coyness. For instance, she wishes she'd slepl with Mall l.eBlanc. 7. She finds significantly younger men "adorable." "Through Playboy I go to nightclubs for promotional events, and I'll be the only person there over 30," she laughs. "I'm bombarded by all these guys in their 20s trying to get my atten­tion. We dance on the bar until two or three in the morning. It's so adorable " v You may have met her online already. In her six months of celibate singledom she has dipped into some online dating. But you can't exactly go on Match.com with the handle cindymargolis. "I did find a couple of people 1 liked on the Inter­net," she confesses. "But when I told them who I am, they completely changed." '.I. She regrets past coyness. Yes. this was also point number six, but she keeps com­ing back to it: "1 was—whatever you might call it—righteous or moral. I think of all the casting-couch opportunities I turned down and 1 ask myself. Would it really have been so bad? I could have been 10 times more famous if I had just slept with the right peo­ple. And il I knew then what I know now. 1 probably would have done it." 11). She cannot play poker. Sure, she won big in the World Series of Poker, but she was trying to lose. "Pam Anderson was having a party that night," she recalls. "I thought I'd be eliminated early, but I just kept winning. I ended up at the final table, but all I wanted to do was go change into a sexy dress to go to Pam's party. So I just started going all in, every time. I scared the shit oul of those guys. I would practically not even look a( my cards. I would just say. "Whatever—all in.' And I could not lose. "

I I. Her whole career has been much like a card game she can't lose. "I get by on

luck and cleavage." she says, still talking poker. But she also tells us. "Every job I got since I was 19 I thought would be my last." She was in the right plate at the right time. She kept things family-friendly and managed to build a career on the sanely beach of the early www. "Thank God for AOL." she says. "If not for AOL, I would not be sitting here talking to imamioy." 12. Even in nudity she remains family-friendly. "The first time I posed for HAYitoY 1 did a signing in Times Square," she recalls. "Families came to it together— fathers, sons. moms. 1 hear from fathers, guys who've collected i'i.ayiioy their whole life, who tell me, 'This is the only time my son and 1 agree on anything.' It's heartwarming and weird. My nudity brought them together. It's like the only thing they can talk about is my boobs." I:?. She gives the people what they want. "When I go on TV I ask the camera­men how they're shooting me.' she says. "They'll say. 'From the head up." I'm like, "No. You've got to show the gold! Shoot below the boobs. It's always boobs up. Why would you want to hide that?'" II. She gives a man what he wants. "I'm very good in the bedroom." she says with a knowing laugh. "I have skills." Such as? "I don't know if you can write this." We can write whatever the hell we want; we're I'Iayboy magazine, Cindy. "Well, my husband came up with the name SMBJ—the Super Margolis Blow Job."

15. She won't be having more children, but she wants to help you have them. She wrote a book about fertility and all that, and if you were to read it, you might become better informed. "It has two chap­ters on vaginas alone,' she notes. "I get to go on talk shows and talk about penises and vaginas and sex positions." This priv­ilege is shared by Dr. Ruth Westheimer, who is not nearly as nice to look at as Cindy—and there's the rub, so to speak. Read her book or don't; she just wants you to get your li'l swimmers tested. "I did i'iayboy for you," she says, address­ing all the men in the world. "Women go through all sorts of shit. We get shots, we get poked and prodded, and half the time the problem is the man's. Men get the fun part: Just go in there and give your sample. Take my piayiioy with you. I'm naked, and I'm here to help you. Your wife can help too—whatever. Just give your sample. II il takes my taking my clothes oil, I'll do it to help families out there. I'm helping America!"

16. She regrets past coyness. Yes, this was point number six and point number nine. But she's still not sure we get the picture. "I didn't lose my virginity until after high school," she says with a sigh. "I always joke that I'm going to tell my girls to be sluts in high school. I'm going to tell them to have fun."

The magnificent

Ms. Margolis is going

to the Mansion. She

just needs a date

16 THINGS KNOW ip v ......

JUS

To enter our contest to win a date with Cindy, visit playboy.com/cindy.