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Imagine trying to buy a pack of gum ($1.50) and being told by your date that you’re not allowed to pay for it. For about a month in the fall of my freshman year, I dated someone who picked up the tab for everything — and I mean everything.

We started off as friends. In fact, I’m not even sure when our friendly outings for coffee turned into three-hour-long dates. Initially, I gravitated toward him because of our mutual love for the city. We both came from bustling metropolises where going out to eat wasn’t just a daily occurrence — it was a ritual. When campus began to seem a little too small, we would both leave FitzRandolph Gate far behind us for Teresa’s ($40), Witherspoon’s ($70), MoC MoC ($100 — it was a lot of spicy tuna rolls) and, occasionally, Mezzaluna ($60). It never really compared to the urban lifestyle we had both been used to throughout high school, but it felt good to go out and see something new when the University grounds began to feel monotonous. It was like it was our mission to eat at all the places off-campus that the Princeton cabs would take us — he refused to travel by bus. To this day, my friends still consult me if they want to eat at a restaurant off-campus, because they know I’ve probably been there before.

I thought it was bizarre when he wouldn’t even let me pay for something small like a pack of mints or the ice cream we would almost always have after dinner ($3), not to mention the fact that we never split the tab despite my many attempts to chip in. Sometimes my friends would ask me how I knew he was wealthy, as opposed to just shelling out the last of his cash to try and impress me. My response was always twofold: If you doled out close to $100 a night for dinner, you couldn’t not be wealthy, and there was one week where we went out every other night. Also, after he’d known them for a couple of weeks he’d tell anyone that his family practically owned a small country.

That was the interesting thing about him. He clearly thought he was the best thing since sliced bread ($1.50 per pound), and my friends didn’t exactly approve of him. But his snarky sarcasm and aloof sense of humor reminded me of my friends in high school. It felt good to be able to keep up with his sharp comments and throw them back at him.

One of my male friends became convinced I was just dating him because he was so wealthy, to the point where my friend would look at me reproachfully every time I came back from one of our dinners. “Do you still offer to split it every time?” he asked me once, barely hiding the disapproval in his tone. “He’s such a jerk that there’s no way you could be dating him for any other reason.” My girl friends seemed to be more understanding. “When a guy isn’t really that nice to anyone but you, you feel pretty special,” one of them admitted to me one day.

The truth is, I wasn’t entirely sure why I was dating him. I’m still not really sure. I thought a large part of it was that he reminded me of what my lifestyle in the big city used to be like, except heading out to grab lunch at the local sushi joint with my friends after school ($20) wasn’t exactly the same as getting dressed up to go to Elements for a three-course affair ($100). He also made me laugh, but so do the guys on “The Big Bang Theory,” and I don’t really have the urge to date any of them.

I think, in the end, what really drew me to him was that he took me seriously whenever I suggested we do something crazy. I had never been with anyone who was so ready to abandon the time pressures of Princeton to go on a random adventure, like the time we got our fortunes told at the palm-reading place off Witherspoon on a whim ($50). The fortune-teller told him that he had come from a world of strong monetary support and many diverse opportunities, and that he would be cared for financially all his life. We came out of the place awestruck by her accuracy until I realized that while looking at his palms maybe she couldn’t help but glance at that sparkly golden watch on his wrist ($10,000).

I’m still not completely certain how and why things ended between us. We had just finished dinner and were heading back in a cab, playfully arguing about where to get dessert, when one of us said, “the city.” The next thing I knew, we were on the train, ready to blow off our classes the next day to spend the rest of the night roaming around New York. When we were safely back in the Bubble, I sent him a text to confirm the plans we had to study together that day, but I somehow knew that he wouldn’t respond and that it would be the last text that I sent him.

I can never really be sure why he wanted it to end, but I know why I did: Visiting the Big Apple made me realize just how guilty I’d been feeling the whole time. Though I knew I wasn’t dating him just because he had a lot of money, at the same time I couldn’t deny in my heart of hearts that it was nice being with someone who could more than afford to fuel my nostalgia for city life. My guilt from never being allowed to pay peaked when I was in the city. I realized that no matter how much I liked his personality, I would never be able to overcome that nasty, nagging feeling I had, that worry that had been voiced directly or indirectly by so many of my friends: that I only liked him for his money.

Of all the things I learned in my freshman year, dating someone as wealthy as he was left me with at least one life lesson: The next time I go on a date with someone, I’m paying.

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