Dating a Guy from the Other Side of the Tracks

We like to think we live in a classless society, but the harsh truth is that class divides still remain. And nowhere can this be a bigger issue than in our dating lives, where intimate topics like lifestyle and finances can sometimes make or break a relationship.

I realized I had been dating within my class when I started seeing my ex-boyfriend. Before him, I had never noticed a spending disparity between myself and my exes. But with this guy, it was a whole different story. I was painfully aware of his wealth every time we went shopping together and he could blow $5,000 on a jacket, or when he didn’t flinch at an expensive restaurant bill. Not to mention his casual name-dropping of famous family connections and multiple homes. But none of this was exciting or impressive. In fact, it was downright unsettling.

The moment I remember most clearly was near the end of our time together. I had referred to someone I knew in passing as “rich.” He held up his hand and said, “Oh, honey, no. We don’t say rich. Cake is rich. We say wealthy.”

I was too shocked to say anything. It was more than just a word choice, or a salary gap between us. It was a divide in cultures and backgrounds, in expectations and habits.

Though our class difference was not the main reason we stopped seeing each other, it was certainly a contributing factor. I was intimidated by his lifestyle and bank account, and never felt we were truly equals. At times I even felt blatantly condescended to, which left me frustrated and insecure.

I know more than a few Cinderella/Cinder-fella success stories exist, and I still believe two people can be compatible and fall in love no matter their bank statements. But shared backgrounds and experiences are important foundations for a relationship, and in this case they were a big, fat wedge.

My major mistake was keeping my insecurities bottled up and letting them fester. Perhaps dating on the other side of the tracks would be easier if discussing class-related differences wasn’t so taboo in our society. Because, let’s face it: class disparities exist, whether they’re between Main Street and Wall Street, or our own bedroom sheets.

-Megan Willett

Girl Talk Time: Have you ever dated someone wealthier than you? Less well-off than yourself? Do you think these types of relationships are common? Do you think they can be successful?

15 Comments

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  • Karmele:

    Wow it tough to be you.

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    1. Thulio:

      girl just take baths and use dareoodnt just be cool and your self around the opposite sex

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  • penda:

    A lot of people say opposites attract. I have been it a similar situation where the guy would always correct my choice of words. He would also have a commenraged about how slow I consume my food.

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    1. Alexia:

      just b uelsrf and try to stay cool…..use lots of deoderent and use like body splash or something like that, that smells excellent.

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  • legem735713:

    I’ve never dated a guy who was rich,but I think someone’s background shouldn’t matter.

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  • smitaarun:

    Before I got married I lived in the lap of luxury, my dad was very well off . I married a guy who didn’t have money , I loved him to death for how he was. I had faith in myself being educated and in my husband that we will make it with hard work . people gave us six months after we got married. Our hard work together and our faith in each other conquered everything and now we are living a pretty comfortable life where I have everything that most people desire.

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  • ceemoney23:

    I have had the pleasure of dating within, above and “below” my class. I must admit that each and every experience was full of the same fun and pitfalls! The deciding factor is not the wealth of the person I choose to date, but the amount of the fun and smiles I get from the relationship. Yes, being able to enjoy the perks of dating a wealthy man is a plus, but I have experienced the most joy from dating men with same or smaller bank accounts…as we get older its about the fun times. I’ve learned to be my own “sponsor”.

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  • Joy:

    I’ve dated people that don’t have as much formal education i.e. dropped out of college. I think it’s more about things in common than anything else. We had different values too.

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  • lumeih:

    dating someone wealthy sounds fun until it actually happens. It would probably make me insecure.

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  • avatar
    hm murp:

    never been in this situation

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  • pepp:

    i’ve never been in a relationship like this , but i’m sure it could work, if both people had true feelings for each other.

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  • Crispy:

    Never really dated anyone that different when it came to “wealth” but I do know some that are.

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  • penelope:

    wealthy not rich? wow :0

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  • sunnytam:

    Never been in this position (sadly). From my years of seeing local society goings-on and reading upper-class mags (Nob Hill Gazette, Gentry, Town & Country), I know that the rich — er, wealthy live in a very different world from you and I. (They shop at Goodman & Bergdorf, I shop at Goodwill.) That insight has at least helped me in my nonprofit volunteer duties when interfacing with, well, not the truly wealthy, but at least the very well-to-do.

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  • avatar
    noki22:

    I have never dated anyone wealthier than I. I want to say when ever I have dated that individual and myself were on the same level of wealth but I do think they can be success if an individial is wealthier than the other. It depends on the person’s personality.

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