This is the first book I’ve read of Jennifer Crusie’s chick lit novels and I liked it a lot. It fit my reading need at the time, which was something short and fun because I knew Harry Potter and the Half Blood Prince was on its way to my door within a few days.

Reading this book reminded me of the teeny-bopper movie, She’s All That, except that this was a version for adults. As the title suggests, the book is about gambling. Not just making bets for money, but gambling on the risks in relationships.

The heroine in the book is named Min Dobbs, and I liked her immediately. She’s a chubby girl with a quick wit, and she knows it. She’s got the same insecurities that all chubby girls have, and she really thinks that the only man who could ever want her won’t be anything like the type of man she would want or be able to get. She’s so sure of this, she’s decided she’s just going to get a cat and forget men altogether.

We learn all this when we meet Min in a bar as her boyfriend of two months, David, is dumping her because she hasn’t slept with him yet. They part their ways and stay at separate ends of the bar. As Min gets consoled by her friends and swears off dating, David joins a group of men that he knows through work. One of the men, Cal Morrisey, is handsome, popular with the ladies, smart, and successful, and he’s always driven Min’s ex crazy with jealousy. David decides to make a bet with Cal just because he knows he can’t win it: pick up Min Dobbs, get her to sleep with him in less than an month, and he wins $10,000.

Cal, as handsome and popular as he is with women, isn’t a chauvinistic pig and he refuses the bet. He says that isn’t the type of bet he likes to take. As an example, he says he might bet $20 that he can pick her up and get her to leave with him for dinner. In the noise of the bar, David doesn’t understand that Cal has refused his bet, instead he thinks Cal is just so cocky that he’s making another bet on top of it. He takes the dinner bet as he’s just as sure that Min wouldn’t leave with any man tonight, not even one as good-looking as Cal, so soon after the heartache of their breakup.

Unbeknownst to either men, Min’s friends have decided she needs to get right back into the game. They’ve scanned the room, spotted Cal, and convinced her to go over to him and ask him out to dinner in front of David, just to show him she’s not heartbroken over him. Reluctantly, and after much pushing, Min makes her way across the bar to ask Cal out. When she gets there, she hears the last part of their conversation about the dinner bet. Fuming, she goes back to her friends, ready to say yes when Cal comes over to ask her out, determined to figure out a way to get back at the both of them.

To make his friends stop needling him, Cal reluctantly goes over to Min to ask her to dinner, thinking she looks like a nice enough person and spending time with her tonight must be better than spending the rest of it with David. Much to his surprise, she agrees, not knowing it’s just so David will lost his bet. They leave the bar, go to dinner, and have a horrible date.

She insults all his pick up lines and calls him on the bet, demanding the $20 he won from David. He feels insulted by her, but mostly small and horrible that she knows he wouldn’t have asked her out otherwise. At the end of the date, Cal (being the gentleman he is), walks Min home. He should be glad it’s over, but he’s got a funny feeling inside. Here is a girl that, when she isn’t insulting him, seems to have a great wit and makes better conversation than he’s had in a while. He’s even noticed that while she dresses blandly, she’s wears great shoes and has cute feet. And she isn’t afraid to really eat in front of him, something most women won’t do on a date with him. He’s noticed all these little things and he’s confused: could he possibly be attracted to her? But she says goodbye, pushes the door shut in his face, and it’s over. Min decides she’s glad the date is over because she won’t have to deal with another man, and Cal decides he’s better off without a girl that insults him every few minutes.

But through coincidence, chance meetings, and a discovered mutual friend, Cal and Min suddenly start bumping into each other more often, and inevitably they start thinking about the other more often. Enough to start showing up in places they’ve seen each other before, just to see if pursuing someone so different and seemingly unavailable might be worth his gamble and her risk of another failure.

This is a novel that is just plain fun to read. The events flow into each other well, and the characters are likeable. The story gets a bit ridiculous and even unbelievable at times, but you forgive Crusie because you laugh enough and look forward to every chapter along the way.