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Hillary Wilkes is the unlikely middle-aged heroine in this romantic comedy about a woman whose life is a precarious climb on an uphill battle.

Toronto, early 2000's. Hillary "Lary" Wilkes is an emotionally and physically challenged, Over Fifty, once a very vibrant woman. She's at the lowest point of her life, having lost her dream job to a younger woman, her self-esteem, and even her sense of humor. Hillary is overweight, underloved and, as a result, feels unlovable - except perhaps from her family, whose encouragement keeps her from bottoming out.

But enough of the self-pity: this is the year she will find herself an exciting new career, lose the 20 pounds for good and find the perfect mate. Quit smoking. Sort out her finances and ... well, maybe she can't do it all at once. But with the help of her best friend Becks, her wonderful neighbor Howard, her lovely niece Pumpkin and her loyal brother Roger, and the cheery encouragement from a new friend Dudley, she knows she can do it. One step at a time.

With a hitch here and there and plenty of fun and hilarity, Lary reaches for the hilltop. But can she find the perfect job, and the perfect man?

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Chapter 1
CHAPTER 1 “Ouch!” Lary winces as she tweezes yet another stray hair from her chin. She peers into the Mirror from Hell, a 10X magnifying circle of terror, weaving atop a flexible metal stem, like God’s ugliest flower. The base balances precariously on the edge of a cigarette-burned counter. She sits on the toilet seat, scanning her jaw line for further insults to her fifty-five years. “What the …?” She tugs on a quarter-incher with her fingers. Scrambling for her tweezers, she knocks over her glass of Cabernet. She grabs the closest towel and mops wildly at the spreading wine. After tossing the red-soaked terrycloth onto the bath mat, she storms from the room. Without slowing down, she manages to snatch the tabby peacefully sleeping on a rocking chair of cast-off clothes. Pizza, named for Lary’s favorite food, meows predictably before settling into her arms. For some reason known only to the cat, he loves the ancient ratty housecoat described by her last boyfriend as her “I-never-want-to-have-s*x-again” robe. Lary finds on the floor what she’s looking for – the rest of the wine. She pours herself another glass with one hand, tossing a month’s worth of tabloids from the sofa with the other. Finally, she manages to arrange both herself and the cat on the down-starved cushions. Without ceremony, the cat kneads her lap for a moment before dozing back to sleep. Lary sucks back the glass of wine. Glancing down at her mid-section, she’s shocked to the bone. Well, not to the bone exactly. More shocked to the fat. “How in the world have I managed to put back all that weight?” Her scale must be wrong, surely. After all, it was just a cheapie from the dollar store. But is it possible? She has put back those twenty pounds? Again? “That’s the fourth time this year!” But on the other hand, she calculates on her fingers, she has lost them four times, which is eighty pounds. She has lost eighty pounds! Well, that sounds kind of good, doesn’t it? Eighty pounds? That’s like one supermodel. She takes a large gulp of wine to celebrate her enormous loss of eighty pounds. Now, okay, let’s see though … she has gained it back … oh, rats … four times. Which puts her right back where she started a year ago. I give up. A soft creaking sound irritates her ears. Bleary-eyed, she turns her head left to find the source of the annoyance. A fake pine tree lists to the right, threatening to topple over, dropping all of its decorations, such as they are. She tries to ignore it, lights a cigarette, and leans back to stare out the tenth-floor windows of her one-bedroom apartment facing south down Yonge Street. Wet snow blurs the view. Lights twinkle. And a double line of honking, angry traffic snakes up the slish-slushy slope south of St. Clair on the late afternoon of December 24th, 2004. “So, I have lost and gained eighty pounds. What else happened last year? I have applied for 1,437 jobs, give or take.” Her fave application had been to conduct cross-country tours for seniors on VIA Rail. But the powers that be couldn’t see how being a downsized television producer made her a successful candidate. “No imagination, honestly! What were some of the other ones? Long distance truck driver. One teeny-weeny problem there – no trucker’s license, but still, a few lessons could have fixed that. Those people were so rude. “Let’s see, what else sticks out? Landscaper, now that was a cool one. Free exercise, after all. What else?” She had considered becoming a hairdresser, a mortician, a pet psychologist, and an electrician. And don’t forget, a zookeeper. The problem was they all required courses some of them even college courses, for Pete’s sake! Small wonder I’ve ended up as a real estate assistant. Not even an agent, just a lowly assistant. Lary strokes the cat. “Start thinking about New Year’s resolutions and have them handy for next week. After all, I have been very successful in keeping my one resolution last year. I have given up swearing. You know, using profanities like my all-time favorite – the f-bomb. It has been a struggle I have to admit. Swearing is one of the great pleasures of life.” And miraculously she has managed to stick to it for a whole year! Lary giggles. “That’s because I have so much fun creating my own swear words. And no one, well, a few do, know I’m swearing at them.” She yells, waking the cat, “Hey, you great kumquat! It’s almost Christmas. What the popcorn?” She drinks some more wine. The new swear words are all food related. That makes it easier to remember. “Okay, this year, what are going to be my new resolutions? Give up chocolate? Sure, why not. Give up ciggies, again? Absolutely. Maybe I should give up … alcohol? The thought makes her whole body shudder. Then she wouldn’t have any flaws at all. And what’s more boring than a goody two-shoes? Little Miss Perfect with a “P.” Nobody likes that. No, she would keep her alcohol flaw but make a concerted effort to cut down on the amount. That’s it. She would moderate herself. Lary glances down and catches sight of her hairy legs; she has forgotten to shave again. What has happened to her personal hygiene? Never mind. Next year will be better. New body, new job. Let’s make that new career. Oh, and a new man in her life. In that order. Lary relaxes her head back on the sofa. “Hey, when you’re on rock bottom, Pizza man, there’s only one way to go, and that’s up, right?”

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