What’s Her Ideal Valentine’s Day Date in Newport?

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The Prep

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In a nutshell:

The ultimate WASP who lives and dies by Lilly Pulitzer floral prints and bright colors. She loves to gossip about her college friends and her crazy aunt’s family in Middletown. Collects monogrammed tote bags like it’s her job. She supposedly has a real job working for her father’s successful firm in New York City, but she spends way more time planning her social calendar.

What she’s wearing:

Whatever the model was wearing in the latest Ralph Lauren advertisement

How you met:

Through mutual friends at The New York Yacht Club while watching the Annual Regatta

Ideal Valentine’s Day Date:

It’s an all or nothing affair for your princess. Two-dozen red roses, a box chocolate covered strawberries from The Newport Sweet Shoppe, the most expensive Hallmark card and the newest KJP arrival are all simply expected. Dinner and champagne at the Clarke Cooke House are also a given. Exuding over-the-top charm is what will truly make your Gossip Girl beam, since it’s probably what won her over in the first place… That and your understanding of her logic that more is more.

The Independent

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In a nutshell:

She’s the definition of the phrase “strong, independent woman.” She works for a start-up based in Boston, but enjoys working remotely in whichever coffee shop she chooses. Prefers dogs over people. Lives and dies according to her iCal. She could eat you alive if she wanted to, not so unlike that South Korean shark in the aquarium.

What she’s wearing:

A crisp white shirt, a tailored blazer, dark jeans and a pair of leather loafers. Not to be confused with The Prep.

How you met:

A networking event for Social Enterprise Greenhouse and Worldways Social Marketing

Ideal Valentine’s Day Date:

She would rather spend the commercial holiday by herself, but she’s putting up with it for you. You have no idea what you’re doing, because she already organized the plans the way she wants it—she’s only letting you drive to indulge your manhood.

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