How did ym get good-girl Mandy Moore to show us her wild side? Easy—we dragged her to the beach and dared her to do wacky things to many, many unsuspecting people. Read on to see which challenges she was willing to face—and which she wimped out on.

Mandy Moore got her first kiss playing truth or dare. "I was about 11, and that game was always the coolest thing," she recalls. “I’d tell my friend beforehand who I wanted to kiss and couldn’t wait to start." Despite this proof that Mandy (now 17) can be a huge fan of dares, she’s not always so adventurous. Until now we’ve seen a Mandy Moore that’s all sugar: sweet songs such as "Candy" on her 1999 debut album, So Real; non-belly-baring videos; and a super-friendly attitude for everyone who hung out on her MTV show last summer.

But there are some signs that she’s branching out a bit. After living in Orlando, FL, almost all of her life, Mandy just bought a swank new pad in L.A. (either her mom or dad stays with her while the other is back home with her younger brother). This summer she’s hosting another MTV show, Mandy, which will feature a mix of music-industry info with wacky sides of celebrities. In August Mandy busts into movies playing a hair-pulling school snob in The Princess Diaries. And she’s let her hair go back to its natural dark blond. (A girl pop star who’s not platinum-blond? How will the world deal?)

So with the release of her new album this month (technically her third, counting last year’s special edition album, I Wanna Be With You), we wanted to make sure her wild side was getting enough of a workout. Our scheme: a day of dares on California’s Venice Beach Boardwalk. Mandy gamely agreed, but her feelings about it could pretty much have been summed up in the world "yikes." "Sometimes it’s cool to be the center of attention, but that’s not me all the time,” she explains. "Most performers really love that, but it’s totally different when you’re onstage."

We propose our dares; some she agrees to, others are a definite no-go. Then we ask her to attempt most of them on the Venice Beach Boardwalk—a unique mess of tchotchke shops, mimes, junk food, speeding skateboarders, and cute boys (more on them later). On we go to activate her inner daredevil, and of course, to pry some truths out of her along the way.

Truth #1: Mandy’s shy about baring her belly.
"I’m usually so self-conscious showing any skin," she says. "I don’t think I can pull it off." When she’s on the beach she wears a tankini or bikini top with shorts. Oh, Mandy, Mandy, Mandy. You look like a model. So what’s the deal? "It’s just that I’m 17 and still growing into my body. I haven’t learned how to love it yet. My arms are too long. My legs are too long. I don’t like my stomach. Nothing seems like it’s right yet!" We decide we should help her gain some confidence. And what a coincidence—we need a cover girl for our swimsuit issue.

Dare #1: Wear a bikini on our cover.
As Mandy flips through the racks of clothes at our shoot, she choose some cool bikinis—as well as sarongs and beach coats to cover them up! She emerges in a killer white Richard Tyler bikini top and matching short-shorts, with an orange mesh sweater over it. When she first steps in front of the camera, she’s more reserved than a table at a chi-chi restaurant. But 10 minutes after the shutter starts clicking, she’s whipping off the cover-up and working it like Gisele. Don’t expect a Britney-style striptease at the next MTV Video Music Awards, though. "Sometimes it’s just so much more elegant and sexy to leave something to the imagination," she says. "Showing your stomach or cleavage can look like you’re trying too hard." Anyway, the high-maintenance aspect of it all discourages her. "I couldn’t be the little sex kitten in every photo shoot and interview," she says. "It’s so much more work than just being myself." Cool—Dare #1 is done.

Truth #2: Mandy’s first single was "Candy."
Her manager bought her a cotton-candy machine for her to use at home.

Dare #2: Hand out cotton candy to everyone on the boardwalk.
This one seems simple at first. We load up Mandy’s arms with as many cotton-candy cones as she can handle. The only snag is trying to keep the cones upright as they sag under the weight of the candy, making Mandy’s hands sickly sticky. "The sugar’s melting all over me!" she shrieks. Gross, but nothing a wet napkin can’t clear up. The bigger problem happens soon after. Let’s put it this way, don’t ever underestimate how crazy boys can get when (1) they’re offered free cotton candy, (2) a pretty girl is handing it to them, and (3) a camera is capturing the whole thing. The three little boys Mandy first approaches are returning from a bodysurfing session. They hyperactively tackle each other to get to the candy, inadvertently knocking Mandy around. Leaving them to wrestle among themselves, Mandy offers some cotton candy to four guys her own age. She’s a tad shier about approaching them, so we enlist our energetic photographer. The guys saunter over, playing it cool (yeah, like they’d rather hang by their bikes instead of have body contact with a hot girl). Unlike the other boys, these guys aren’t jumping on her, but our guess is they’d die to. Mandy hands the remaining cotton candy to a few girl fans who ask for her autograph. She seems much more comfy with them.

Truth #3: "I’m in love for the very first time and it’s the most exciting feeling in the world!"
Mandy’s been dating Wilmer Valderrama—the high-larious exchange students, Fez, on That ‘70s Show—since last fall. "We’re like the sickeningly lovey-dovey couple," she gushes about her first serious boyfriend. "It’s ridiculous. My grandma even likes him. She thinks he’s the cutest thing in the entire world." When they met at a photo shoot, Mandy had never even seen Wilmer’s show. “The only TV I watch is MTV. But I’m glad I hadn’t watched his show because I probably would have thought he was the biggest dork." Despite each of their crazed schedules they get to see each other pretty often. (After our shoot she was primping to go to a taping of his show later that night.) And when she’s on the road, Mandy says, "He surprises me in airports, flies to cities to see my show, brings me dinner at my place. He took care of me when I got my tonsils out. He couldn’t be any more perfect." Her only cause for pause, she tell us, is that he’s older—she wouldn’t even give us his age. (He’s 21; we have our ways of finding this stuff out, Mandy.) Who cares, though? "I’m so happy just to sit in my pajamas and my glasses with no makeup on. I’m so comfortable around him and don’t feel like I have to impress him anymore, which is so cool," she tells us. "Dating someone hilarious who does comedy as his work has made me open up. I’m letting myself laugh more."

Dare #3: Have your tarot cards read.
Exploring life’s mystical side is another first for Mandy. We find a tarot reader on the boardwalk and wait for her to finish revealing the future to her current customer. She’s taking forever. Come on! Mandy ponders what question to ask: "Will my album do well?" (Could be interesting.) "Will I be lucky in love this year?" (Could be more interesting!) Finally, the customer leaves and Mandy plops down in the chair next to the reader. She goes for the love question. The bad news is that the cards show that Mandy’s man will develop some issues that could dampen the flame. "She said it’s going to go well probably through the year," Mandy reports. "But then we’re going to have problems and we’ll break up after that. That’s a bummer because I’m really happy right now. I just don’t want to know or worry about the future. So I was kind of freaked out." Bummed, freaked—whatever. Mandy’s not gonna let any tarot lady ruin a good thing. "I don’t want to jinx it by worrying and making something happen that shouldn’t," she says, morphing back into happiness.

Truth #4: Mandy’s never worked at a fast-food place.
In fact, she’s never had any waitress experience since her singing career boomed before she was old enough to fill out a restaurant application. After going to a musical theater camp at age 9, singing became her focus, and she got some gigs belting out the national anthem at Orlando sports events. A few years later, she was discovered by Sony while doing voice-overs for commercials. Even though she’s now also employed by MTV (we hear they pay a little more than minimum wage), Mandy confesses she’s always wanted to work at McDonald’s. Um, what? "Then I’d learn to loathe it and never eat there anymore," she explains. Not even the fries?

Dare #4: Take orders from behind the counter at a fast-food joint.
We stake out a place and very, very sweetly ask Pedro, the man peering out at us from the order window, if we could not only have some lemonade but also help him serve it. He’s a little confused, but shrugs and lets us through the back door. Now on the other side of the food world, Mandy slowly gets her bearings—lemonade dispenser, massive oil vat for fries, greasy stove where hot dogs are sizzling. At first, she’s not dying to bust over to the window and ask the customers what they want. "I feel like I’m in the guys’ way, and they’re like, ‘Who’s this stupid girl trying to do our job?’" We remind her it’s part of the dare deal, so she laughs a little, throws up her hands, and takes an order for chili-cheese fries. People trickle in: a little girl who wants ice cream and two teenage boys who Mandy finds out are visiting from Canada (who cares what they want to eat—they’re cute). As customers line up, shouting in orders from the front and side windows, she slowly gets into the groove of barking the orders into the kitchen. Most customers don’t even recognize her (amazing how hunger blinds these people!). The only area in which she’s lacking is getting people to cough up the cash for their food. She’s collected a total of one dollar for the numerous chili-cheese fries, hot dogs, and lemonades she’s doled out. We wind up paying Pedro $40 to cover any losses.

Truth #5: Mandy’s less outgoing offstage than she is when she’s performing.
"Usually if I went to the boardwalk with my friends, I’d be very quiet," she says. "I’m definitely not the one in the group who would run up and just start dancing and singing with people. I’d be the one laughing in the background." Oh yeah?

Dare #5: Sing backup vocals for street performers.
It’s nearing the end of the day and Mandy’s getting pretty tired, so we’re thinking it might be time to wrap. Enter Betty and Elton White, street performers who are cranking out Vegas-style lounge tunes on a vibraphone. Betty’s silver-sequined dress and corkscrew ribbon earrings (not to mention Elton’s scary thong) are eye-catching, to say the least. Then it hits us—Mandy should join their act! We run it by her. "Oh gosh, do I have to do this?" she giggles. "Are people going to laugh at me?" But soon she’s in. "There comes a point when you’re like, ‘Who cares?’ I’ll have fun. I bet people wish they were up here doing what I’m going to do!" Betty and Elton have never even heard of Mandy Moore, but they couldn’t be more psyched. They get set for their next song, A Horse With No Name. Since that song came out in 1972 and Mandy came out in 1984, she’s not an expert on the words. No problem. Her hand claps, ooh-aahs, and bouncy enthusiasm carry her through the song. The large crowd that has gathered to listen seems more than entertained as they crack up and snap pictures. After the song and heartfelt good-byes to our new buddies, Betty and Elton, Mandy gives us her assessment of the performance. "Okay, first of all, both of them were singing to completely different songs! She was screaming ‘la, la, la’ in the microphone, and I just repeated her. I felt like Tom Green," she says. "It was really fun though. I got a little self-conscious when the crowd started to form, but they obviously enjoyed it." The only negative: "I couldn’t live up to Elton and Betty. They were genius!" And with that, our Day of Dares is finally done! "This was so much fun. Most magazine stories are boring," says Mandy. "It was definitely a good growing experience. I got to see a side of myself that I’m too scared to let out sometimes." We’re just psyched to have helped unleash her fearlessness. Who knows—maybe she’ll dare us sometimes.

10 Dare Mandy Wouldn't Dare Do:

1. Go to Tower Records and sing her own songs at a listening booth
2. Bury a stranger in the sand on the beach
3. Wear a blue wig into Coffee Bean and Tea Leaf to order her favorite coffee
4. Hand out samples of pigs-in-a-blanket at a grocery store
5. Let YM answer her cell phone for the day
6. Get a tattoo
7. Get a body piercing
8. Send roses and fake loves notes in her name to Justin Timberlake, Nick Lachey, and Jorge Santos (Christina’s [Aguleria] boyfriend)
9. Call Marilyn Manson and ask him for advice on how to be a goth chick
10. Be the assistant to our Editor-in-Chief Annemarie for a day