A Complicated Woman: Dating Insights from a Heartfelt Escort

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“Pretty Woman” unleashed its unique brand of romantic chaos on the world 25 years ago, on March 23, 1990. At just 15, I found myself stuck in the early stages of dating, having yet to experience the thrill of a boyfriend, a first kiss, or even the awkward moments that come with them. The romantic comedy genre was just beginning to regain its footing following the success of “When Harry Met Sally” the previous year. Once “Pretty Woman” graced theaters and grossed an impressive $463 million, rom-coms surged in popularity—Hollywood doubled its output from the ’80s to the ’90s—and with no personal dating experience to draw from, I relied on “Pretty Woman” and its numerous imitations as my go-to guide for love.

I can hardly remember my teenage years without “Pretty Woman” influencing my perspective, which feels like one of those dramatic statements made by Julia Roberts’ character, Vivian. She grapples with her feelings for Edward Lewis, the wealthy businessman portrayed by Richard Gere, who hires her for a week as his “companion.” For years, I wasted time in unhealthy relationships, self-defeating thoughts, and emotionally unavailable partners, all while overlooking how profoundly this movie shaped my skewed views on romance. The film’s impact on my dating habits is undeniable.

I’m not just referring to the surface-level tropes, like the “hooker with a heart of gold” stereotype or the notion that love is about a woman needing rescue. Though “Pretty Woman” has faced criticism for its outdated gender norms, its exploration of relationships is surprisingly contemporary. The romantic banter in classic Hollywood often reveled in the playful battle of the sexes. In contrast, the dialogue in “Pretty Woman” is rife with passive-aggressive jabs. Edward mocks Vivian’s profession with lines like, “You make $100 an hour and you’ve got a safety pin holding up your boot?” These comments come after she saves him from a precarious situation, underlining a troubling dynamic.

When Edward and Vivian argue in the penthouse suite, it mirrors the blowouts I had with boyfriends for years. “I’m sorry I ever met you,” she snaps, even though her feelings tell a different story. These are the phrases we use when we want our partners to chase after us, to engage in the drama we think we want. After a disagreement, I often found myself wanting to test my partner’s commitment by acting as if I would walk away.

While movies shouldn’t only depict perfect conflicts, the absence of healthy communication can lead to years of misguided expectations about relationships. It fosters the belief that fights are about saying everything but what you truly feel, relying on your partner to intuit your needs. “Pretty Woman,” in many ways, misled me about what a real disagreement should look like—turning it into a battle for dominance rather than a pathway to understanding.

Vivian embodies the archetype of the “Manic Pixie Dream Girl.” She’s a free spirit who knows about cars and enjoys casual dining, yet her character hints at the exhausting task of molding oneself to fit someone else’s desires. Edward frequently judges her, leaving her feeling inadequate. His compliments are veiled critiques, reminding me of the subtle ways some men can manipulate their partners’ self-esteem.

Despite my own strong will, I often found myself drawn to men like Edward: charming, intelligent, and self-serving. The mental gymnastics required to maintain these relationships were exhausting. I felt like the damaged one in the dynamic, often blaming myself for our issues and attempting to meet their unspoken expectations.

What frustrates me most about “Pretty Woman” is how it trivializes Vivian’s desire for a genuine relationship. Her longing for equality with Edward is presented as a whimsical childhood fantasy rather than a legitimate aspiration. In the end, when Vivian states she’ll “rescue him right back,” I wish she had instead tossed him off her balcony.

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In summary, “Pretty Woman” shaped my understanding of relationships in ways that I didn’t fully recognize until later. Its portrayal of love and conflict may have been entertaining, but it also perpetuated damaging stereotypes that influenced my romantic choices for years.