Dear Sidewalk tells the story of Gardner, a 24 year old mail-carrier, who is struggling to contend with his identity as his quarter-life crisis is in full swing. His regimented routine is thrown out the window when he meets Paige, a divorcee, enduring a mid-life crisis of her own. In this relationship there exists a synchronicity, as they find, despite their age difference, they're both confronting existential problems surrounding identity, love, and the choices in front of them.
Three childhood friends - Elise, Sonia and Cecile - leave for a summer in the South of France to help clear Cecile’s holiday house before it is put up for sale. There, they soon become the prime targets of three horny young men, for whom these single forty-year-old women are much more attractive than girls their age.
Holly Golightly is an eccentric New York City playgirl determined to marry a Brazilian millionaire. But when young writer Paul Varjak moves into her apartment building, her past threatens to get in their way.
After a high-profile firing, everything is at stake for 40-year-old Jenna: her career, her ticking biological clock, and her bank account. Her fashion career comeback hits a snag when she falls for a charming, much younger coworker — who happens to be her boss’s son. As sparks fly, Jenna must decide if she’ll risk it all on a secret romance with the one person who could destroy her comeback.
The young Harold lives in his own world of suicide-attempts and funeral visits to avoid the misery of his current family and home environment. Harold meets an 80-year-old woman named Maude who also lives in her own world yet one in which she is having the time of her life. When the two opposites meet they realize that their differences don’t matter and they become best friends and love each other.
Mother Nature loves to cause mischief, and she steps in to help two love-starved souls find happiness. She helps an aging professional woman and single mother, Rosie, who's unlucky in love find her match with Adam, a much younger man. As their relationship blossoms beyond physical attraction, matters complicate when her adolescent daughter starts to fall for a handsome local boy.
Teacher Linda Sinclair balances her staid home life with an incredible passion for her subject, but her routine is forever altered when a former star pupil and his unsupportive father reenter her life.
Upon discovering her husband's infidelity, Sandy leaves the suburbs and moves into the city. There, she befriends Aram, a guy whose wife only married him so she could get a green card. Sandy hires Aram to be her nanny, and it isn't long until Aram and Sandy find out they get along wonderfully and start to date. But is their relationship real or is it, in fact, just a rebound for both of them?
After 20 years of marriage, Maria decides to leave her husband. She moves into room 212 at the hotel across the street, with a bird’s-eye view of her apartment, her husband and the life she shared with him. While she wonders if she made the right decision, many of the people in her life offer their opinions on the matter. They intend to let her know, whether she likes it or not, on what proves to be a life-changing evening.
Julia Lambert is a true diva: beautiful, talented, weathly and famous. She has it all - including a devoted husband who has mastermined her brilliant career - but after years of shining in the spotlight she begins to suffer from a severe case of boredom and longs for something new and exciting to put the twinkle back in her eye. Julia finds exactly what she's looking for in a handsome young American fan, but it isn't long before the novelty fling adds a few more sparks than she was hoping for. Fortuately for her, this surprise twist in the plot will thrust her back into the greatest role of her life.
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