Best movies like The Worst Year of My Life

a film about letting go...

A unique, carefully handpicked, selection of the best movies like The Worst Year of My Life Starring Trevor St. John David, Amy Vorpahl, Cate Beehan, Nicholas Tucci, and more. If you liked The Worst Year of My Life then you may also like: Office Space, Over Her Dead Body, Ruby Sparks, All My Life, The Secret Sex Life of a Single Mom and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

One week before proposing to his girlfriend, Kyle, a down-on-his-luck romantic, discovers that she's been sleeping with another man. Unemployed, saddled with debt, and depressed, Kyle embarks on a funny yet affecting journey to recovery that involves living in his car, bottom-of-the-barrel jobs, therapy, online dating, and Kyle's own wild, fantastical, and snarky imagination.

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Office Space

A depressed white-collar worker tries hypnotherapy, only to find himself in a perpetual state of devil-may-care bliss that prompts him to start living by his own rules, and hatch a hapless attempt to embezzle money from his soul-killing employers.

Over Her Dead Body

After his fiancée, Kate, dies in an accident on their wedding day, veterinarian Henry grows depressed. To help him move on, his sister has him visit psychic Ashley and gives her Kate's diary. Ashley uses the journal's details to convincingly deliver the fake message that Kate wants Henry to move on. However, Kate's ghost is watching over Ashley and Henry. Furious when they fall for each other, she vows to sabotage their relationship.

Ruby Sparks

Calvin is a young novelist who achieved phenomenal success early in his career but is now struggling with his writing – as well as his romantic life. Finally, he makes a breakthrough and creates a character named Ruby who inspires him. When Calvin finds Ruby, in the flesh, sitting on his couch about a week later, he is completely flabbergasted that his words have turned into a living, breathing person.

All My Life

It was a chance meeting started by one of Sol’s friends trying to chat up Jennifer. However, in the end, it was those two who hit it off. Sol enjoyed Jen’s smile, her effort, and how silly she could be. Jen enjoyed Sol’s cooking, his athleticism, and that he would join her in fun moments. As you can imagine, love bloomed, and things got serious. Jen’s investment in Sol led to her pushing him to follow his dreams and even move in to save money. Sol’s investment in Jen well, it led to him proposing. But what started as a liver tumor grew into full-on cancer, so with a diagnosis of 6 months to live, Sol and Jennifer try to make the best of it.

The Cleanse

The story of a heartbroken man who attends a spiritual retreat, only to discover that the course releases more than everyday toxins and traumatic experiences.

Thanks for the Memory

Steve Merrick is an out of work writer who stays home and plays house husband while his wife goes to work for her former fiancé and Merrick's publisher who is still carrying a torch for her.

The Sisterhood of the Traveling Pants 2

Four young women continue the journey toward adulthood that began with "The Sisterhood of the Traveling Pants." Now three years later, these lifelong friends embark on separate paths for their first year of college and the summer beyond, but remain in touch by sharing their experiences with each other.

Forgetting Sarah Marshall

When Sarah Marshall dumps aspiring musician Peter Bretter for rock star Aldous Snow, Peter's world comes crashing down. His best friend suggests that Peter should get away from everything and to fly off to Hawaii to escape all his problems. After arriving in Hawaii and meeting the beautiful Rachel Jansen, Peter is shocked to see not only Aldous Snow in Hawaii, but also Sarah Marshall.

Ashley

A teenage girl, distraught from her vain attempt to connect with her estranged mother, resorts to cutting herself. When she develops an online relationship with an older woman, she learns to accept her sexuality and the endless solitude of sprawling suburbia.

Twice Upon a Yesterday

Victor Bukowski is an out-of-work actor with problems. He's got a lousy agent, he has a habit of falling out with directors and he's still in love with his ex-girlfriend. However, Victor is about to embark on an unexpected emotional journey which will make him confront his future and his past mistakes.

My Name Is Joe

Two thirtysomethings, unemployed former alcoholic Joe and community health worker Sarah, start a romantic relationship in the one of the toughest Glasgow neighbourhoods.

Thanks for Sharing

A romantic comedy that brings together three disparate characters who are learning to face a challenging and often confusing world as they struggle together against a common demon—sex addiction.

Two Night Stand

After an extremely regrettable one night stand, two strangers wake up to find themselves snowed in after sleeping through a blizzard that put all of Manhattan on ice. They're now trapped together in a tiny apartment, forced to get to know each other way more than any one night stand should.

Man's Castle

An unemployed man turns to crime when he gets his girlfriend pregnant.

The Health Journey

The film is about the health resort Granhedsgården in Dalarna, Sweden, and they have a problem. They don't have many guests at all and something must be done. At the same time, Stig-Helmer is a little depressed after his girlfriend has left him, and so he lives on junk food. His best friend Ole invites him to come along to the health resort Granhedsgården. Now, the craziness begins.

My Dead Boyfriend

Mary’s life has been defined by a string of temp jobs and a half-hearted attempt to become a writer. But all that changes when she comes home to find her boyfriend dead in front of the TV set. During her misadventures in trying to get rid of his ashes, Mary discovers that there was much more to her couch potato boyfriend than she ever thought imaginable.

Rumi: Turning Ecstatic

In December 1997, Tina Petrova drove off a cliff - literally and figuratively. A tragic car crash in the California desert was the beginning of a journey that would lead her to the extraordinary works of 13th century Sufi mystic Mevlana Jellaludin Rumi and to a remarkable array of people whose lives have been transformed by his poetry and philosophy. Rumi: Turning Ecstatic is her true story, a timely, powerful docudrama that take the viewer into the very heart of Sufi mysticism.

Christmas Cupid's Arrow

Holly, a professor at a small college, has had a long history of finding the wrong guy. She’s accomplished quite a bit in her life, but after her younger sister announces she is pregnant, Holly decides she is going to make an effort to meet Mr. Right. Meanwhile, David, another professor, is a single father, very smart and kind, but not the type that Holly takes notice of when the two are assigned to plan the Christmas Formal. At the insistence of her best friend, Holly signs up for the dating website “Cupid’s Arrow,” where she meets Josh, an attorney just hired by the school. He’s everything she wants on the surface, but has little to say beyond his work and good looks. Josh and David were roommates in college, so Josh recruits David to write poetic messages in an attempt to win Holly over.

I Believe in Unicorns

Follows the lyrical journey of an imaginative teenage girl who runs away from home with an older punk rock drifter, but not even unicorns can save her now.

Mid-Love Crisis

The week of her 50th birthday, Mindy, a divorced teacher, is going through a bonafide mid-life crisis as she prepares to host a long weekend at the lake with former boyfriend Sam, ex-husband Marc, and daughter Rita and her girlfriend Emily. In the process, Mindy begins to discover what it is she truly wants as she gets ready to start the next chapter.

Love on the Vines

When overworked lawyer Diana’s (Margo Harshman) uncle, Hugh, passes away she’s called back to his vineyard to settle his estate. Hugh has left half of his Golden Range Winery & Vineyard to Diana and half to Seth (Steve Talley), his right hand man and Diana’s ex-boyfriend. Hugh’s final request is that the two work the next harvest together, set to begin in a few weeks. Neither is happy at the arrangement but they begrudgingly agree. Furthermore, neighboring competitor Grant Garritson (Jack Wagner) threatens to drive a wedge into Diana and Seth’s already shaky relationship. They have a short window to figure it all out so that they both get what they ultimately want.

Hearts of Spring

A famous mommy blogger faces an empty nest as her daughter prepares to go away to college. When she turns to her blog for advice, she finds herself on the attack by a reader who has conflicting opinions. While she deals with him online, offline she finally meets a great single dad and sparks start to fly. What she doesn’t know is that the confrontational reader and the adorable single dad are, in fact, the same person.

My Awkward Sexual Adventure

A hyper-repressed and schlubby accountant (Jonas Chernick) strikes a deal with a worldly but disorganized stripper (Emily Hampshire): he'll help her with her crushing debt if she helps him become a better lover.

Late Bloomers

Louise, an aimless, 28 year-old Brooklynite, recently single, sort of a musician, depressed without admitting to it, drunkenly falls while doing something stupid and breaks her hip. This lands her in a physical therapy ward full of people twice her age. There, she meets Antonina - a cranky elderly Polish woman, who speaks no English. Louise gets a job caring for her. Neither woman loves the arrangement but it’s time to face the truth about aging. We all have to grow up sometime.

The 10 Year Plan

Myles and Brody are best friends with two very different ways of finding love. Displeased with their current love lives, they make a pact to be together if neither finds love in ten year’s time. Now two months shy of their deadline, both friends set off to do whatever it takes to avoid ending up as each other’s last resort.

Just in Time for Christmas

Lindsay is faced with a life-altering decision as Christmas approaches: Stay in her tiny hometown and marry boyfriend Jason or accept a coveted post teaching at an Ivy League college on the other side of the country. What to do? Fortunately for Lindsay, she has some big-time help in the form of a magical messenger who is able to transport her three years into the future to see how it would all turn out.

Are You Happy Now

An unemployed man-child strives for happiness by proposing to his marriage-averse girlfriend, and taking a job at a run-down chicken joint.

Something Always Happens

Unemployed car salesman Peter is encouraged by his girlfriend Cynthia to approach the head of a petrol company with his plan for making petrol stations more attractive to customers. When the man rejects the idea Peter joins a rival company and becomes a great success.

Melody Gardot: The Accidental Musician

Jazz sensation Melody Gardot's grief-stricken, yet inspirational, journey to stardom is captured in this inspiring documentary. After being struck by a car in 2003, an accident that left her with life-altering injuries, Gardot began the emotional expedition towards healing. This special follows her path to recovery, intimately revealing how she used music as therapy to heal her spirit and ultimately impress the world. Featuring candid interviews and performances of her most famous songs from albums "Worrisome Heart" and "My One And Only Thrill".

Rocky Road

When a Wall Street firm downsizes, a well-to-do trader finds himself living with his parents and driving their ice cream truck.

The Heart Machine

A man begins to suspect that his long-distance girlfriend, whom he met online but has never met in person, has been living in the same city the whole time and sets out to find her.

A Love to Remember

After a year of interacting exclusively online, Tenley, an eco-conscious horticulturist, finally works up the courage to meet her online crush, Jared. When Jared doesn’t show because of a bike accident, Tenley gets mistaken for his wife at the hospital. Soon, she’s forced to keep the lie up with Jared’s entire family and his annoyingly charming best friend, Everett in order to save Jared’s company… You’ve Got Mail meets While You Were Sleeping!

Love’s Match

Smart and beautiful matchmaker Leah Price is the owner of dating website Soulmatch. But when one of her clients still doesn’t find love, Leah reluctantly agrees to allow devilishly handsome rival matchmaker Peter Beckett, whose speciality is arranging romantic meet-cutes, to help her.

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