Top Movies & TV Shows Similar to Boss Wants a Happy Ending List

• The Proposal - Romantic comedy involving a boss and employee relationship, where fake romance leads to real feelings.
• How to Lose a Guy in 10 Days - A romantic comedy centered around a bet that complicates a blossoming romance.
• The Intern - Features an unexpected relationship between a young employee and their seasoned boss.
• Crazy, Stupid, Love. - Intertwined romantic stories that involve confusion and unexpected relationships.
• Two Weeks Notice - Romantic comedy about a boss-employee relationship where personal dynamics complicate professional ones.
• 33 Postcards - A mix of romance and personal discovery that explores relationships across different contexts.
• 13 Going on 30 - A magical romantic comedy that explores love and personal growth with a lighthearted twist.
• Notting Hill - A love story between an ordinary man and a famous actress, filled with comedic moments.
• 10 Things I Hate About You - A modern adaptation of Shakespeare’s Taming of the Shrew, focusing on romance and youth.
• To All the Boys I've Loved Before - Teen romantic comedy involving fake relationships that lead to genuine romance.
• Bridget Jones's Diary - A humorous diary-based film that deals with love, self-acceptance, and societal expectations.
• Friends with Benefits - Explores the complexities of a casual relationship turning into something deeper.
• The Wedding Planner - Centers around the tension between a wedding planner and the groom, full of romantic twists.
• Summer Catch - A summer romance involving unexpected relationships and personal growth.
• Love & Other Drugs - A romantic drama that delves into a relationship complicated by personal challenges.
• Love Actually - Multiple intertwined love stories that capture the essence of romance and relationships.
• Sweet Home Alabama - A romantic comedy about rediscovering love amidst personal dilemmas and farm life.
• Eat Pray Love - A story of self-discovery through travel and relationships, exploring love and personal growth.
• The Ugly Truth - A battle of wits between two romance-focused characters leads to unexpected romance.
• What Women Want - A story about understanding the opposite sex and the romantic entanglements that follow.
• My Best Friend's Wedding - Romantic comedy where a woman realizes her feelings for her best friend just before his wedding.
• The Wedding Ringer - A comedic tale about friendships and unexpected relationships leading up to a wedding.
• Hitch - A relationship expert struggles with his own feelings when helping others find love.
• The Other Woman - Explores the unexpected bond between women caught up in a love triangle, with comedic elements.
• 27 Dresses - A romantic comedy about a woman always in love with her best friend, revealing personal challenges.
• Legally Blonde - A determined woman shows resilience and self-growth, with a side of romance.
• She’s All That - Romantic comedy about transformation and unexpected feelings, wrapped in high school drama.
• About Time - A whimsical take on love and time travel that explores deep relationships among characters.
• The Last Five Years - Musical romance that examines a relationship's rise and fall in a unique narrative structure.
• Definitely, Maybe - A romantic comedy that explores different paths in relationships and love through storytelling.
• The Five-Year Engagement - This comedy dives into the long journey of a couple trying to make their engagement work.
• Your Place or Mine - Unexpected encounters and relationship dynamics unfold when two long-distance friends swap homes.
• Before We Go - A chance meeting leads to an exploration of relationships and personal connections over a night in the city.
• It's Complicated - Explores love, re-igniting romance, and relationships involving complexities of adult life.
• Someone Great - A hilarious and emotional exploration of relationships wrapped in a coming-of-age story.
• Love Wedding Repeat - A chaotic wedding day leads to various romantic mistakes and unexpected relationships.
• The Switch - A woman's life takes a turn after a casual relationship leads to unexpected parenthood.
• The Perfect Date - Centres around a young man offering a service to be a date, leading to unforeseen romance.
• When We First Met - A man gets a chance to relive a night and change his romantic fate, leading to comedic outcomes.
• The Kissing Booth - A teen romantic comedy revolving around a love triangle and high school shenanigans.
• Aloha - A romantic film exploring love, ambition, and personal relationships against a beautiful backdrop.
• 10 Things I Hate About Life - A romantic exploration of young love and life challenges involving strong emotional ties.
• How to Be Single - A fun exploration of single life and relationships among friends in a lively city.
• Palm Springs - A unique romantic comedy exploring relationships and time loops with humor and depth.