"You're so granola," David would tease. I'd shrug it off as good-natured, but when he met my mother, and they both began ribbing me about my appearance, I felt it was time I reassessed my style. I started to blow out my curly hair, once my defining feature. I began to actually pay attention to what I wore each morning, even smeared on some makeup once in a while. All so, when in his world, I could stop feeling like a ratty pair of Hanes adrift in a sea of La Perla.

Needless to say, my mom was thrilled that I had met a handsome, well-to-do Jewish man with serious intentions. All my life, my mother had worried that I was too smart, too fat, too rebellious to meet and marry a guy she would approve of—and like. When I brought David home, she swooned. "This is a man," she proclaimed.

"This is a man to marry." Though I hated to admit it, I had to agree with her. Don't get me wrong: David and I still had our issues. And sometimes the lifestyle divide between us felt as wide and deep as the Grand Canyon. After all, while I stressed about paying off $30,000 in college loans for the next 15 years, David spent that much on a monthly vacation.

I was hyper-conscious of the spending gap between me and David, and I never wanted to give off the impression that I was taking advantage of his wealth. In fact, when he offered to buy me a new Mac during our first month together, I politely but firmly declined. But never was the difference between our worlds so vivid as the day we went shopping for ski pants. The saleslady ignored me but spotted the red Prada tag on David's ski jacket in a nanosecond— and promptly brought him the matching pants. They cost $600.

"They match my jacket," said David. "It's a no-brainer." I referred him to the $80 variety, but he was already waving his black AmEx around. "Do you really need those?" I asked. "What's need?" he answered. I was hurt and infuriated by his callous comments. If only he knew how much I could have used $600. Though my family lived in an affluent community, my parents were struggling; my dad had recently been diagnosed with cancer. Soon after, his garment business had tanked.

"Don't be stupid," my mother told me, when I relayed the story. "If he is generous with himself, he will be generous with you." And he was. Still, I couldn't help seething over the fact that David didn't know what it was like to pay for a bagel and soda with a credit card—and be declined. That he didn't know what it was like to have creditors call him all day or to have his cell phone cut off because the bill hadn't been paid. When I would hint at my financial problems, David would dismiss them. My family appeared well-off. I had graduated from Columbia.