A Troubled Romantic’s Guide to Dating: Lessons from a Heartfelt Streetwalker

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Updated: May 18, 2020
Originally Published: March 22, 2015

A quarter-century ago, on March 23, 1990, Pretty Woman premiered and introduced a fresh, albeit flawed, perspective on romance. At just 15 years old, my own love life was a blank slate: no boyfriends, no kisses, and certainly no awkward romantic encounters. This was also a time when the romantic comedy genre was starting to emerge from a dry spell, thanks in part to the success of When Harry Met Sally. After Pretty Woman grossed an astonishing $463 million, the rom-com became a staple in Hollywood, doubling in production during the ’80s and ’90s. With no dating experience of my own, I turned to Pretty Woman and its countless imitators for insights on relationships.

I honestly can’t recall my teenage years without the influence of Pretty Woman. This realization may sound melodramatic, but Julia Roberts’ character, Vivian—an engaging streetwalker navigating her feelings for the suave businessman Edward—has shaped my understanding of relationships. For years, I grappled with self-defeating thoughts and unhealthy patterns without recognizing how deeply this film impacted my perspective on dating.

I’m not merely critiquing the film’s surface-level elements, like the clichéd “hooker with a heart of gold” trope or the notion of a woman needing a man’s rescue. While Pretty Woman has faced criticism for its outdated gender dynamics, its exploration of relationships is surprisingly contemporary.

The film’s dialogue often mirrors the passive-aggressive exchanges seen in social media and dating shows today. Edward’s quips about Vivian’s profession, such as mocking her income while simultaneously relying on her for companionship, reflect the unhealthy dynamics I later encountered in my own relationships.

Take, for instance, their fight in the penthouse suite. Vivian’s dramatic declarations of wanting to leave while remaining still echo the sentiments I’ve expressed during my own arguments. Such scripted conflicts often distort what healthy communication should look like, making it easy to carry unrealistic expectations into real-life disagreements.

Despite her quirks, Vivian embodies a form of the “Manic Pixie Dream Girl,” a trope that continues to evolve. She’s a character who seems to be tailored to cater to male fantasies, and her experiences serve as a reminder of the exhausting effort many women, including myself, have put into meeting the expectations of men. Edward’s condescending remarks about her appearance only amplify the struggle of seeking validation from someone who doesn’t truly appreciate you.

I, like Vivian, found myself drawn to charismatic yet emotionally unavailable partners. The subtle manipulation from men who seem charming at first can take years to recognize, leaving you feeling like the “damaged” one in the relationship.

Furthermore, what frustrates me most about Pretty Woman is how it trivializes Vivian’s desire for an authentic, equal relationship. Her longing for more than just material comforts is often dismissed as a fairytale wish, echoing the notion that women should conform to certain romantic ideals.

In the end, while the film has its merits, it also presents a distorted view of love and conflict that can lead to confusion in real relationships. Perhaps, instead of seeking a “rescue,” the focus should be on mutual respect and understanding.

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In conclusion, Pretty Woman may have entertained audiences, but it also left a complicated legacy, shaping many of our expectations of romance in ways that are often less than constructive.