Movies Like The Trouble with Bliss
If you loved The Trouble with Bliss's Comedy and Drama storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks

Greenberg
Roger Greenberg, a failed musician now making a living as a carpenter in New York, returns to Los Angeles to house-sit for his brother. He's stranded there—since he doesn't drive—until his brother's assistant, Florence, comes to his rescue. She's as much a lost soul as he is, and the pair form a significant connection—giving Roger a much-needed reason to be happy.

A California Christmas: City Lights
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.

Peace, Love & Misunderstanding
A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.

The Best You Can
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.

How to Please a Woman
When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.

Cyrus
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.

You Will Meet a Tall Dark Stranger
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.

Happythankyoumoreplease
Captures a generational moment - young people on the cusp of truly growing up, tiring of their reflexive cynicism, each in their own ways struggling to connect and define what it means to love and be loved. Six New Yorkers juggle love, friendship, and the keenly challenging specter of adulthood. Sam Wexler is a struggling writer who's having a particularly bad day. When a young boy gets separated from his family on the subway, Sam makes the questionable decision to bring the child back to his apartment and thus begins a rewarding, yet complicated, friendship. Sam's life revolves around his friends — Annie, whose self-image keeps her from commitment; Charlie and Mary Catherine, a couple whose possible move to Los Angeles tests their relationship; and Mississippi, a cabaret singer who catches Sam's eye.
More Movies Like The Trouble with Bliss

Cosi
Lewis, a young amateur theater director, is offered a job with a governmental program for the rehabilitation of mentally ill patients in a Sydney institution. His project is overrun by one of the patients, who wants to stage the opera Cosi Fan Tutte by Mozart, despite the fact that none of the patients can sing or speak Italian. A comedy of errors ensues, but one which unifies the patients and their director in unexpected ways.

Love & Sex
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.

He Said, She Said
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.

Father of the Bride
A father comes to grips with his daughter’s upcoming wedding through the prism of multiple relationships within a big, sprawling Cuban-American family.

Love Don't Co$t a Thing
A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.

Sidewalks of New York
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.

Numb
Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel, lesbian exercise classes and a dizzying variety of pills get him through the day, but don't quite solve his problem. His writing partner tries everything to get him back to normal, but it's not until Hudson meets Sara that he finds a real motivation to get better and to actually start feeling again. From the writer of Deuce Bigalow, comes NUMB, a romantic comedy following an unusual man looking for strange love.

The Giant Mechanical Man
An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.

XX/XY
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.

Cherry
Ivy League Freshman, Aaron Milton (17) gets a different kind of education when he falls for Linda (34) a vivacious former wild-child who has returned to college to straighten out her life. The curriculum gets more challenging when Aaron meets Linda's sarcastic 14 year-old daughter, Beth - who quickly develops a crush on him. The math doesn't work in either direction but the dysfunctional triangle becomes a learning experience for all involved.

(Untitled)
A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art.

Coyote Ugly
Graced with a velvet voice, 21-year-old Violet Sanford heads to New York to pursue her dream of becoming a songwriter only to find her aspirations sidelined by the accolades and notoriety she receives at her "day" job as a barmaid at Coyote Ugly. The "Coyotes" as they are affectionately called tantalize customers and the media alike with their outrageous antics, making Coyote Ugly the watering hole for guys on the prowl.
Why These Movies Are Similar
These recommendations share core qualities with The Trouble with Bliss (2011): Comedy and Drama themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of The Trouble with Bliss.
See full details for The Trouble with Bliss (2011)