I live in a famous building on Fifth Avenue owned by a certain publicity loving billionaire with a bad pompadour. One year ago, I had no health insurance and lived with my parents in Brooklyn. What happened?

It's simple, really: I fell in love with a man who is out of my age—and tax—bracket. Some people would call me a trophy wife. At times, I, too, have wondered if that's what I've become.

When I met David at a party of a mutual friend, I was a 21-year-old Jewish girl with a freshly minted Ivy League degree in philosophy, accustomed to being unimpressed by the guys who approached me. So when David sauntered over and offered to buy me a drink, I was indifferent. My friends quickly sidled up to whisper that he was quite the catch—a notorious heartbreaker. Unmoved, I blathered on pretentiously about a trip I'd taken backpacking through Italy. David called me on my affected spewing, in Italian no less.

As luck, or the fates, would have it, he'd lived with an Italian family for six months in college. It worked—I was charmed. Offering to drive me home, he walked me up to a glistening silver Porsche. "This is your car?" I asked. I'd been on dates before with boys who drove Porsches—but Porsches purchased by their daddies, and driven by guys who moved way too fast. David, in contrast, drove me home, then sat with me in my parents' driveway, just talking, for hours.

From that night on, we were inseparable. It scarcely seemed to matter that I was a short, slightly depressed aspiring novelist working as a secretary, while he was a tall, trim, 30-year-old owner of a well-established fashion house, high on the ease with which things came to him. And our other differences—the nine-year age gap, the fact that I made less money than his maid—were, at best, laughable to us. Within two weeks, we were meeting each other's families.

"She's the first girl I don't have to dumb down for," he told his mother. For me, being with David was a relief. My previous boyfriends had left all of the planning and decision-making to me. Every time I saw David, he had a surprise in store: reservations at a new restaurant, wind-blown rides on his Ducati motorcycle, a room full of candles and our song—U2's "Trash, Trampoline and the Party Girl"—on repeat. We compared the books we'd read; discussed philosophy, religion, life; and marveled at the fact that we’d found each other.

We spent those first weeks happily ensconced in our bubble, so it wasn't until we began to socialize again that I realized just how ill-equipped I was to be his girlfriend. In my old life, I had gone to rock concerts, crowd-surfed, and carefully cultivated my grungy anti-style. Now, as soon as I stepped into his building's posh elevator I morphed into a dowdy nerd next to the army of models and actresses with their Chanel bags and expertly coiffed hair. I felt self-conscious; David's friends' wives all shopped at Barneys. My "designer" pieces came from Nine West and H&M.