When love and money come together, things can get somewhat confusing. That’s why we decided to find out for ourselves what it’s like to pursue the wealthy in the age-old art form of being a gold digger.

Debbie Harry poses with a sign that says "Sex Object."

The running joke is that women often prefer men with an excessive cash flow. But many of us would be shocked to know that websites focused solely on pairing wealthy men — i.e., Sugar Daddies — with almost always significantly younger women is perfectly legal. With site names like, Seeking Arrangement, Seeking Millionaire or Sugar Daddie.com, you are bound to be at least a little bit skeptical as to the credibility of these establishments, asking whether or not the U.S. government is in the process of investigating these sites for human trafficking… But before all of you active users on these sites start cursing and pointing fingers at your computer screens, because there are more working gold diggers out there than I had initially assumed, here me and most of the community of supposedly ignorant pop culturists out. Because I can’t speak for everyone and their own moments of discovering this what-should-be-underground phenomenon, I can only describe how I felt upon learning about this scenario, which was an overwhelming feeling of intrigue rather than disbelief. So with new sense of curiosity, I decided to find out more of what it’s like to date a wealthy benefactor. Because I was scared shitless of doing it myself (obviously, I could very well use the money…), I started my exposé by asking people who have already participated in these types of relationships.

Chloe, 23 — I like the casual nature of this type of relationship. It’s very NSA (no strings attached), often discrete and mutually beneficial…It’s rather empowering.

They call their love a “mutually beneficial relationship” because each party has something of worth to offer to each other. For one person, it’s their money, while for the other, it’s their time and charm. As the description on Seeking Arrangements says in regards to “Sugar Babies” — the younger counterparts in these relationships, “You know you deserve to date someone who will pamper you, empower you, and help you mentally, emotionally and financially.” And for the site’s registered Sugar Daddies, a description states, “Some call you a mentor, sponsor or benefactor. But no matter what your desires may be, you are brutally honest about who you are, what you expect and what you offer.”

Antoinette Andrea, 25 and How to Bag a Baller blogger  — People are sometimes judgmental about the idea of dating up until they realize that it’s not about using someone or being taken advantage of…It’s about finding someone whose company you truly enjoy, and if you happen to reach a point in life where you need some help, you already have someone who you trust that is there to help you.

But for the most part, the partners in these relationships are not exclusive to each other, which leads many to ask — how can this be allowed, and where is the line drawn between prostitution and actual dating?

Marilyn Monroe acts in Gentlemen Prefer Blondes

Chloe — With married men, they understand if you have outside romantic interests, which I enjoy. There are some who are okay with it, as the idea of an NSA relationships is not to allow attachment and drama to permeate the relationship. Of course, doing so you have to be careful for health reasons. Communication with your serious romantic partner is also important, as no one needs that bad karma.

For Antoinette Andrea, living in NYC is difficult enough for most young people in their twenties. On her blog, How to Bag a Baller, she discusses the main premise for going after the affluent, which is more focused on self-worth and the total belief that one deserves the best because you are the best. Like her site describes, “Tired of being disappointed by DJ’s, bartenders, and boys in bands? Here is your go to guide for how to date outside your social scene and find someone who treats you exactly the way you deserve.”

Antoinette — Being rich is not a requirement for me to date someone, but it definitely makes living in Manhattan a lot more fun. There are so many things that most young people in the city don’t get to experience regularly, such as world class spas, Broadway shows and eating at the top restaurants in the country. When you date someone who treats you to these things, it gives you a whole new outlook on what living in New York is all about. I think Marilyn Monroe’s character in Gentleman Prefer Blondes says it best: “Don’t you know that a man being rich is like a girl being pretty? You might not marry a girl just because she’s pretty, but, my goodness, doesn’t it help?”

And Brandon Wade, founder and CEO of Seeking Arrangements, Seeking Millionaire, Miss Travel and What’s Your Price.com, believes that it’s okay to judge the opposite sex on a surface-y level at first. “I think all relationships start off in a very superficial manner,” Wade explained to Business Insider. “For men it’s a visual thing. That’s why women upload photos that reveal their skin and show off their figures…Women tend to look at men in terms of how successful they are, what sort of job they have, how much money they make.”

With this in mind, after gaining a brief-ish glance into the world of Gold Digging, I came to realize that beauty is essentially located in the eye of the beholder because maybe financial stability is a prerequisite for some people, while good looks or a connection with someone is another. Dating could very well be considered a game, especially when you figure in the process of asking someone out to dinner, coffee or the effect of a simple text message because of its wording. But when money and sex come together, especially when a relationship is deemed NSA, things get a tad hazy and confusing, leaving many people somewhat angry and righteous because love and dating are two very personal topics to humans everywhere. Who knows what’s “right.” All I care about is the fact that I was so clearly unaware that Gold Digging was a real social phenomenon. Dammit.

[Featured imaged sourced via moviezeal.com. Other images sourced via anonymousaesthetes.blogspot.com and Tumblr. If any of these images belong to you, please let us know because you’re awesome, and we’d like to provide proper credits/remove image(s) upon request.]