Greta Gerwig, who has officially graduated to carrying a lead role on her own, is the ideal casting choice for Lola, a conflicted, vulnerable, recently spurn 29-year-old trying to figure out her next life move. Directed and co-written by Daryl Wein (known for writing and directing 2009's Breaking Upwards), Lola Versus is at times uncomfortable and excruciating, but then, so is life. The film opens with Lola dreaming she is on a beach littered almost entirely with dildos. Chalk it up to the importance of having a man in her life or the imminent realization that she is going to have to fend for herself.

Either way, Lola informs us, "I hate to admit it, but I have an astrology book." In said astrology book, there is a foretelling of cataclysmic change during Lola's twenty-ninth year. Frightened of this concept, Lola asks, "What if I like my life the way it is?" Soon after, change does come--in the form of being proposed to by her longtime live-in boyfriend, Luke (Joel Kinnaman). In the throes of planning for the wedding, however, Luke has a last minute epiphany that he isn't ready for marriage.

Her world shattered, Lola is consoled by her two best friends, Henry (Hamish Linklater), and Alice (Zoe Lister Jones, who also co-wrote this script and Breaking Upwards with Wein). Although Alice does her best to inspire Lola into seeing the positive aspects of her relationship status ("Being single builds character"), Lola cannot seem to function as an unattached entity. This fact becomes especially clear when Alice tries to take Lola to a bar only to witness Lola have an instantaneous panic attack after envisioning all of the potentially gross sex she could have. She tells Alice to hail her a cab and immediately takes it to Henry's apartment, where safety, familiarity, and alcohol reside.

The none too abstruse connection between Lola and Henry is allowed the chance to augment now that Luke is out of the picture. The complications of anything starting between them are, unfortunately, too great to ignore, considering Henry is also close with Luke. Regardless, Lola is too enmeshed in romantic uncertainty to be able to sleep alone at night, inciting her to invite Henry over one night after seeing Alice in an atrocious play called Pogrom!. Instead of falling asleep, Lola ends up making out with Henry, who quickly insists they should take it slower out of respect for Luke. To Lola's dismay, she goes along with the suggestion.

Meanwhile, Luke has been obsessively trying to get in contact with Lola, who has just as obsessively been ignoring his calls. Instead, she tries to distract herself with other offers, even if they do come from prison architects named Nick (Ebon Moss-Bachrach) who seduce with Ani DiFranco music and tout that they have a large penis because they were an incubator baby. Ultimately, Lola succumbs to meeting Luke for lunch, which promptly lands her in his bed. She then comprehends that attempting to see Luke in a casual manner is too emotional for her.

With this revelation in tow, Lola once again pours her efforts into trying to be with Henry, who has already lost faith in her after finding out she had sex with the prison architect. Frustrated and bewildered, Lola does her best to focus on working on her thesis, an in-depth criticism about the presence of silence in literature. As the weeks wear on, Lola finds herself increasingly confounded over who she should be with, not uncovering her inherent knowledge that being alone is the best course of action for her.

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By the time Lola's thirtieth birthday rolls around, she has been through the strife of seeing Alice snap Henry up from under her, Luke dating another woman, and stealing two bottles of Miller High Life to go on a bender that consists of going to a strip club and roaming the streets of New York aimlessly. If that's not rock bottom for a white woman, I don't know what is. In spite of all this, Lola still comes out the other side of darkness, further vindicated when Luke asks her to get back together at her birthday party (that he wasn't invited to). Politely, and in drag queen fashion, she declines by saying, "I'm already taken--by myself. I just need to do me right now."