A Complicated Love Story: Lessons in Dating from a Heartfelt Hooker

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It’s hard to believe that “Pretty Woman” came out over 25 years ago, on March 23, 1990. I was just a teenager, struggling through the early stages of dating—no boyfriends, no kisses, and definitely no chance for those awkward moments that might lead to something more. At that time, romantic comedies were slowly coming back to life, thanks to hits like “When Harry Met Sally” the year before. Once “Pretty Woman” hit the big screen and raked in a whopping $463 million, rom-coms exploded in popularity. With no real-life experience to draw from, I relied on “Pretty Woman” and its many imitations as my unofficial guide to relationships.

Honestly, I can’t think of my younger years without “Pretty Woman” being a part of it. Sure, it sounds a bit dramatic, but like Julia Roberts’ character, Viv, I found myself wrestling with my own feelings about love and relationships. For years, I didn’t realize how much this film shaped my confusing, often messed-up view of romance. It showcased so many of the unhealthy patterns I’d later find myself repeating.

Let’s be clear: I’m not just talking about the clichés of a hooker with a heart of gold or the notion that true love means a woman needs rescuing. While “Pretty Woman” gets critiqued for its outdated gender norms, its portrayal of relationships actually reflects some pretty modern ideas. The banter and tension between Viv and Edward (played by Richard Gere), while entertaining, often feel more passive-aggressive than playful. For instance, Edward’s comments about Viv’s job come off as more mocking than charming.

Their arguments mirror many of my own in past relationships. When Viv snaps, “I’m sorry I ever met you,” it resonates with anyone who’s ever felt hurt in a fight. In my younger days, I often found myself longing for someone to chase after me, to prove they cared. It was like a test, one I thought I had to pass.

Movies shouldn’t always be about showcasing perfect, therapist-approved arguments, but when they fail to show healthy communication altogether, it can lead to years of misunderstanding what conflict should look like. It’s not about saying anything except what you truly feel; it’s about winning the fight instead of finding common ground.

Vivian also represents an early version of the “Manic Pixie Dream Girl” trope, or even the “Cool Girl” type defined in “Gone Girl.” She’s quirky and fun, but it often feels disingenuous as she tries to mold herself to meet Edward’s expectations. Watching her navigate through the judgments and comments from Edward is exhausting. It makes me reflect on how I used to adjust myself to fit what I thought men wanted.

Despite her struggles, Viv is often mocked for wanting a genuine connection. Her wish for a meaningful relationship with Edward is reduced to a naive fairy tale instead of being recognized as a legitimate desire for partnership. And when she claims she’ll “rescue him right back,” I can’t help but wish she’d just toss him out the window instead.

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In summary, “Pretty Woman” may be a romantic comedy, but it also serves as a case study for the complicated dynamics of dating, self-worth, and the quest for genuine connection.