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Flirting with Disaster

About The Book

Felicity is a total romantic. That’s why she follows her heart—not the rules—in her job as a cupid. But when Felicity turns her matchmaking magic on her best friend, Andy, it’s Andy who breaks their golden rule: friends always come first. Andy is so wrapped up in her new guy that she’s ditching everyone else. How can Felicity stop her BFF from letting a BF come between them?

Meanwhile, Felicity decides to get over her crush on Derek by setting him up with someone else—but in her impulsive haste, she accidentally matches him with the whole school, and now everyone is in love with him. The entire student body is headed toward heartbreak, just weeks before prom. Does Felicity have what it takes to make everyone’s heart happy…including her own?


“There are lots of fun ways to have a good time at a party without drinking!” Mrs. Cahill, our health class teacher, hopped up on the end of her large desk. She crossed her legs beneath a flowing brown paisley skirt.

A few people chuckled at her words, and I bit back a laugh myself. At least she was enthusiastic about her topic. It was hard for me to scrape up enthusiasm for anything on a Monday, but Mrs. Cahill never lacked any.

“So, what did you guys list?” Mrs. Cahill asked. “Let’s share a few of our choices with the class. Now as I said before, I won’t be collecting them. This is for you to take home and hopefully implement in your life to encourage a lifestyle that avoids alcohol.”

Yeah, right. I was sure most of my classmates would instantly give up partying because of a list made in health class. That was totally plausible.

I glanced down at my paper. Our in-class assignment was to write ten “fun” things to do that didn’t involve alcohol. Out of my ten items, six of them involved staring longingly at Derek, the guy I’ve been madly in love with since freshman year. No way was I going to say that out loud, though.

James Powers thrust his hand into the air, a smarmy grin on his face.

“Go ahead, James,” Mrs. Cahill said. “What did you write?”

He made a big show of holding up his paper in front of his face. “Ahem. I put, ‘have sex.’”

His buddies around him guffawed, and several girls tittered behind their hands. I rolled my eyes. Mrs. Cahill should have known better than to call on James.

“Oh my God, James!” one girl whispered, giggling. “You’re so crazy.”

Mrs. Cahill blushed and pressed a hand to her beet-red cheeks. “Well, that’s … not quite what I meant.”

Mallory Robinson, my mortal enemy and the bane of my existence, turned and whispered something to her friends, Jordan and Carrie. Jordan nodded briefly in response, but Carrie barely looked at her. They both turned their attention back to James. Mallory’s face fell. She quickly recovered and started writing in her notebook.

I smirked. The dynamics between Mallory and her friends had changed ever since I’d set her up last month with Bobby Loward, a.k.a. Bobby Blowhard, the biggest weenie I’d ever known. It was still the most talked-about love match around school, even though the magic had worn off and Mallory and Bobby had split up a few weeks ago.

Of course, nobody else knew that there’d been magic involved in their hookup, let alone that I was the cupid responsible for the match. Total secrecy was the first rule of my job at Cupid’s Hollow. I wasn’t allowed to tell a soul that my hot-pink PDA was used to matchmake my classmates using the latest in handheld technology—love arrows shot through e-mail.

Not that anyone would believe me if I were allowed to spill the beans. Though maybe the ridiculous pairing of Mallory and Bobby Blowhard would be convincing proof.

Mallory’s friends hadn’t treated her the same since. It didn’t matter that they’d broken up the day the spell wore off. The damage was already done.

My only regret was that I couldn’t step forward and claim credit for what was surely an act of humanity: keeping Mallory’s stuck-up nose out of my best friend Maya Takahashi’s dating life by giving Mallory a relationship of her own to focus on. But the cupid contract I’d signed meant I couldn’t spill the beans—and frankly, I feared my boss Janet too much to screw around with that.

“What about spin the bottle, then?” Mitzi, one of the flaky chicks in our class, asked. “That’s just making out, not actually doing it.”

Andy Carsen, my other best friend, bit back a laugh. She leaned over and whispered to me, “I think the whole point of the exercise was to avoid bottles.”

“No kidding,” I said quietly, shaking my head.

Mrs. Cahill looked over at me. “Felicity, since you feel like talking, do you have anything to add to our conversation? What did you write down on your list?”

Whoops. I glanced at my paper, reading aloud an entry that wouldn’t totally humiliate me for life. “Um, play poker.”

Not that I knew how to play, but I don’t think that mattered to her. At least I didn’t say something that involved being naked.

“Good answer!” Mrs. Cahill beamed at me. “Card games are a fun and healthy alternative to drinking at a party.”

“What an ass kisser,” I heard Mallory whisper to her friends. They giggled.

Andy spun around in her seat and stared hard at Mallory until she looked away.

The bell rang, dismissing us from class.

“Make sure you hold on to those lists,” Mrs. Cahill said loudly over the bell as we all rushed to evacuate. “Especially since we’re nearing prom season.”

“Thank God that’s over,” I said to Andy as we walked down the hall. “I swear, that class gets weirder every day.”

“No kidding,” Andy said. “I don’t think Mrs. Cahill was expecting those responses. She should know James by now, though. He’s always going to give the most obnoxious answers he can think of.”

“You know, I’d feel bad for her if she hadn’t given us this dumb assignment in the first place.”

I hated health class with the fiery passion of a thousand burning suns. It was possibly the most boring, ineffective course I’d taken to date. The only good thing about it was I didn’t have to take gym anymore, one of the other most terrible classes ever.

I was so not athletic, and it was highly unfair that I was forced to participate in events that made me look like a dumbass. Ever see me dribble a basketball? Once you did, you’d understand my plight.

But health class was not much better. For one period every day I was trapped in a room with both James and Bobby. And even worse, with Mallory, who took every opportunity to shoot me nasty glares across the room, or make snotty comments to her friends.

In between shooting me the evil eye, Mallory would sneak peeks at James, who was her boyfriend freshman year. She was probably wondering why they weren’t still together. Um, maybe because she was a total cow. Not that James even noticed her anymore. He was too busy trying to show the whole class how very funny he was.

Fortunately, Andy was in there with me. She helped make the time go faster with her dry humor.

“Hey, Felicity, that was a good answer,” Bobby Blowhard said, appearing out of nowhere and sliding in between me and Andy. “I didn’t know you played poker. What’s your favorite kind? I like Texas Hold’em.”

Fortunately for us, and all of mankind, Bobby wasn’t wearing his usual mesh workout shirt. Instead he had on a tight black spandex top. I suppose it was his way of enticing people to look at his muscles, but I can’t say it worked on me.

“Actually, I don’t really play,” I mumbled, trying not to be rude, but also not wanting to encourage him into further conversation.

Bobby was … overbearing, to say the least. I’d noticed that once the cupid spell wore off him, he lost his attraction toward Mallory and instantly regained it toward me.

Lucky, lucky me.

“Oh.” Bobby paused and flexed a little. “Well, maybe I could teach you sometime. I know lots of card games, actually, and—”

“Hey,” Andy interrupted, “it’s time for us to head to lunch.” She grabbed my elbow and led me away.

“Okay, see ya!” Bobby bellowed to my back.

I gave him a halfhearted wave as Andy and I darted down the hall.

“I owe you,” I told her gratefully. “Cokes are on me.”

We headed to the cafeteria and made our way through the lunch line to our usual table, where Maya was already waiting for us. She was holding hands and talking closely with her boyfriend of almost a month, Scott Baker.

I swear, the guy looked like he had a permanent flush whenever he was around Maya. It was cute, even if it was a little goofy. But it made me happy to see her with a guy who was perfect for her.

After the fiasco of matching her up with three guys at once, I’d learned the hard way that it was much better to do a one-on-one pairing. Much, much better. Maya had started dating Scott after that, and they’d been going strong since. Of course, I had sent them a cupid e-mail to encourage their attraction (not that they’d needed it).

And just as cool, I’d recently received my second bonus check for a lasting love match. Score!

“Hey,” Andy said, plopping down beside Maya. “How’s my favorite couple today?”

“Oh, hey guys!” Maya shot us a big smile. “How are you? Anything good going on?”

“Not too much,” I said. “Except in health class James said he wanted to have sex instead of drink at a party, and Mrs. Cahill about had a heart attack.” I sat on Andy’s other side and started noshing on my burrito.

Maya shook her head. “Yeah, that sounds like him. And more exciting than my morning.”

“Actually Maya got an A on her French test,” Scott interjected. “She beat all of us with the top score. She could probably teach our class and put Monsieur LeBec out of a job.”

Maya shrugged, blushing. “I guess you’re just a good study partner,” she replied. She glanced at her watch, then stood. “Oh, I gotta go. I told Mr. Seagle I’d help him set up the chem lab today before class.”

“I’ll go with you,” Scott said, automatically rising beside her.

“You two lovebirds have fun. Try not to coo all over each other,” Andy ribbed.

Maya shot her a fake glare. “Funny, funny.”

She and Scott headed out of the cafeteria, glued to each other’s sides. I couldn’t help but grin at the sight of them.

“If I didn’t love Maya so much, I’d be super jealous,” Andy said, watching them go. “She looks so happy.”

I jerked my head to look at her. “Jealous? Really? I thought you’d sworn off love.”

Andy bit her lower lip. She drew lines in her creamed corn with her fork. Why the school was serving creamed corn with burritos, I’d never know.

“I thought so too,” she said with a sigh, “but seeing how good they are together makes me think maybe I’m missing out on something.”

My heart rate kick-started to about a million beats a minute. Andy had been on a self-imposed sabbatical from guys for a while now and hadn’t shown any interest in dating. So this was the opportunity I’d been waiting for—to hear her say she was ready for me to find her a love match.

Okay, not that she knew I’d be matchmaking her, but whatever. I knew I could do the job justice. After all, Maya and Scott were still going strong, as were DeShawn and Marisa, an unlikely couple I’d paired on a whim who seemed to beat all odds and make it work. That relationship had also changed DeShawn’s bad attitude, and he wasn’t the überbutthead he used to be.

I just knew I could help Andy find love too.

“Yeah, Scott seems like living proof that there are nice guys out there,” I said casually.

“No kidding. If only we could all be so lucky. She snagged herself a good one.” Andy took a bite of her food, then shot me a pointed look. “Not that you won’t be that lucky soon, with you-know-who.”

My stomach flipped over in excitement at the thought of Derek smiling at me the way Scott smiled at Maya. God, would there ever be a time when Derek didn’t make every part of me feel utterly, painfully alive? A time when I wasn’t a total wreck, wishing I could get him to see me as the perfect match for him?

For the thousandth time since taking the cupid job, I rued the fact that I couldn’t matchmake myself.

“Well, who knows what’ll happen with that,” I said, biting off a big hunk of my burrito. I chewed and swallowed before speaking again. “Our plan of me repeatedly throwing myself in front of him hasn’t seemed to work yet.”

Not only had Derek not fallen head over heels in love and dropped down on one knee to ask me out on a date, things hadn’t progressed much further than the casual conversation stage we had been at for a couple of months now. It was slow torture, and yet I was putting myself willingly through it every step of the way.

“Well, maybe we’ll both be surprised.” Andy shot me a crooked smile. “Maybe love will strike us both out of the blue.”

I grinned back. “If it can happen for Maya, it surely will happen for you.”

Because I’d sure see to it that it would.

That afternoon I made it my primary mission during my classes to select the lead candidates for Andy’s love match. Holding my tricked-out PDA just out of the teacher’s line of vision, I flipped through the profiles I’d stored in it and found two guys I thought might suit Andy and that Maya and I might not mind having around.

First was Tyler Macintosh, a cute guy who plays drums in a local band. He’s popular and always has a big crowd around him wherever he goes. His light brown, wavy hair looks casually tousled without any effort, and he’s always smiling and laughing with his friends. Andy could definitely appreciate his positive attitude and enthusiasm.

The other guy was Jacob Simpson, a superhot, smart guy on the soccer team. I didn’t know much else about him, other than he’s really, really attractive, with big dimples in his cheeks, and black hair. Oh, and a soccer player. Duh, me. Anyway, he truly is the perfect blend of brains and brawn, and Andy tended to like a good combo of both those elements.

Yes, these were promising initial character notes, but I still needed to flesh out their profiles before I chose between them. I wanted to do right by Andy … and to cover my butt with Janet, my boss at Cupid’s Hollow, by making sure the match would meet the minimum compatibility requirements. Luckily, I had classes with both guys, which made it easy to add notes into my LoveLine 3000.

During anthropology, while Mr. Wiley scrawled furiously across the chalkboard, I tucked my PDA into my lap and continued enhancing the profiles I’d created of Tyler and Jacob.

Name: Tyler Macintosh

Age: 17

Interests: Loves music—carries drumsticks everywhere in back pocket. Also into performing, and likes to bang drumsticks on his desk when teacher’s gone. Good sense of humor. He cracked a funny joke today about night-shift waitresses at Waffle House.

And he totally checked out Andy at lunch when she walked by. But then chewed his sandwich with mouth open. Ew! And did “seafood” to another guy. Obviously likes attention.

Style: Casual rocker

Name: Jacob Simpson

Age: 17

Interests: Sports and fashion—likes to wear soccer socks and shin guards, even when not in a game. Into fitness and has nice butt—go, Greenville High soccer hotties! Also checked out Andy at lunch. Gee, surprise.

Made crack about “large” girl in anthropology class. :-(

Style: Preppy sports guy

At the end of the day it looked like seafood and drumsticks won out over tight soccer tushie. While Jacob might have been cuter than Tyler, the fat joke he made wasn’t cool. I felt bad for the butt of his joke, Justine, who’d just stared straight ahead in class and pretended not to hear him.

I shot Jacob a glare when I caught his eye, just to show I disapproved, and I made a mental note never to matchmake him to any of my friends. The jerk.

Yeah, Tyler was the no-brainer choice here. I’d seen Andy check him out once or twice before. Plus, it didn’t hurt that Andy was wild about musicians. She had pictures of drummers from several bands plastered all over her notebooks.

Surely it had to be fate.

I composed my e-mail to Tyler, CC’d Andy, and sent it. When they opened the e-mails, they’d fall in love instantly, matched together for two weeks of bliss.

Awesome. I couldn’t wait to see Andy happy in love.

© 2010 Rhonda Stapleton

About The Author

Photograph © Joanna Laurenzana

Rhonda Stapleton started writing a few years ago to appease the voices in her head. She lives in northeast Ohio with her two kids and their lazy dog. Visit her website at

Product Details

  • Publisher: Simon & Schuster Books for Young Readers (March 9, 2010)
  • Length: 256 pages
  • ISBN13: 9781416974659
  • Grades: 7 and up
  • Ages: 12 - 99
  • Lexile ® HL690L The Lexile reading levels have been certified by the Lexile developer, MetaMetrics®

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Raves and Reviews

"In this silly but entertaining romantic comedy, impulsive but good-hearted Felicity learns how unpredictable love really can be, whether she intervenes or not. This sequel to Stupid Cupid (2009) stands on its own." –SLJ, June 1, 2010

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