Understanding The Other Woman: Talking to a Sugar Baby

As countless couples and would-be romantics prepare for Valentine’s Day, many others are putting in the prep work for the less celebrated Mistress Day, which falls on February 13. In honor of the little-known holiday, I spoke with Jessica, a sugar baby herself as well as a spokesperson for Seeking Arrangement to to better understand the inner-workings of the lifestyle and to shed light on how it works and why people opt for these romantic options.

In the United States alone, there were more than 4.5 million registered female sugar babies listed on SeekingArrangement.com alone last year. Many of these aspiring sugar babies may find themselves out of luck however, as there are only approximately 900,000 registered sugar daddies on the site within the US — not a small group, but in comparison that’s roughly five sugar babies for every sugar daddy.

In 2018, the University of Texas at Austin ranked fifth highest population of college sugar babies, with Texas State University coming in seventh. Photo by Rochelle Nicole

“Traditional dating isn’t for everyone,” Jessica explained. “A lot of people on Seeking Arrangement, in terms of sugar daddies, are divorced; they have kids, sometimes they're separated. A lot of them have been through a traditional relationship and they're no longer interested in that, and they find that dating on traditional dating sites is people looking for monogamy — people who are looking for traditional dating where you’re talking about marriage and kids and your future together. They want to date younger women; women they don't really have access to; women who are going to respect them for being successful and having a lifestyle to provide. On the other side of things, sugar babies are in university or college. A third of them are, and the average age is 26 for a sugar baby and the average age for sugar daddy is 39.”

This fact seems to be a common thread among Texas women, as eight Texas-based colleges and universities were among the top 100 campuses of sugar babies, with the University of Texas in Austin landing in the top five.

“Life is getting more expensive, and beginning your life as a new college grad isn't always easy — getting there isn't always easy,” Jessica explained. “Most people can't pay for college anymore, and in order to graduate with no debt or with any kind of career path it’s sometimes necessary to use your relationships to get there. Can those can be romantic relationships?”

While many college coeds are actively looking for older men to provide for their needs, Seeking Arrangement’s data indicates that most of them won’t be in the lifestyle permanently — almost to indicate that the price of education has become so steep that women would sleep with men nearly old enough to be their fathers just to get a decent shot at the American dream we’re all told exists out there somewhere. Jessica sees this as women being more aggressive in their dating preferences, before they decide to settle into a long-term relationship.

“Most of them are not looking to settle down right now,” she said. “People are getting married later, and a lot of sugar babies find that they don't want to date guys in their age group or guys who are immature in their opinion. They would rather date someone who can provide a certain lifestyle for them and provide mentorship and who isn't afraid take them to nice places and don't care about the price tags — and they’re finding that you can find that with a sugar daddy. They're not looking for a traditional relationship, they're not looking to settle down.”

You may be wondering, by now, who these older men are that are dating and financing these sugar babies. While Seeking Arrangement’s data isn’t precise, according to Jessica, the average income was roughly $250,000 annually, but this number comes from voluntary reporting, so unless you have one of their elite memberships, they’re not checking your tax returns. Jessica also admitted that most guys that are making bank don't disclose their income on the site to avoid the gold diggers — and no, they’re usually not single.

Many sugar babies prefer not dating men in their age group, opting for older, more financially successful men. Photo by JD Mason

“Most of our sugar daddies are married,” she admits. “The option on our site for status is ‘married but looking’ and we aren’t in the business of passing judgement. We expect people to be open and honest on the site, and if somebody is looking for a relationship outside their marriage I think that's their choice and we want them to be honest on the website about that and hopefully honest at home about that, but that's really none of our business as long as the relationship is on your terms.”

While all of this may come as a surprise to many people, Jessica believes that a large part of the shift in culture comes from people having a better understanding of themselves and being more honest about what they want at a particular stage in life.

“Everyone 20 years ago assumed that getting married in a traditional nuclear family was the goal, and for a long time that was a measure of success and the measure of happiness, but that's not the case anymore,” she explained. “People are finding happiness in other ways and people are becoming more honest about that. A lot of people who were married 20 years ago are getting divorced and finding that they don't want to be married again...Previously it was normal to get married at 22, and now that's viewed as young to get married, so I believe as that norm shifts — and people are understanding that your brain is actually not done developing until you're 26 — you can't psychologically make a sound decision until then. People are realizing that you should wait a little longer to dive into a relationship that's going to supposedly last forever. I think people are just being more cautious.”

According to Pew research, the median age for first marriage in 2015 was 29 for men and 27 for women compared to 27 for man 25 for women in 1995. Courtesy photo

It’s often easy for people to hear about these sorts of relationships and look down on the people who engage in them, often lobbing insults their way or referring to them as escorts, but according to Jessica, it’s much more complex than simple sex work. In her experience, it’s more about being open and honest about the expectations and requirements of a relationship that may or may not be mutually exclusive.

“There is a stigma around [sugar dating],where people are honest about the time and money that they want to spent in a relationship, and it's automatically associated with sex work. But in reality all successful relationships have a financial component and hopefully they have a sexual component, and if that's the case then you have to be honest about those things. A lot of people are not honest about the financial expectations and it leads to divorce. About one third of divorces have a financial component as a reason. Someone isn't going to pay your bills and pay your tuition and buy you a new car and take you to Tahiti because you had sex with him. That's not really how it works. You have to build a relationship in order to get someone to actually be generous with you, and sugar daddies aren't donating to charities.”

If you’re wondering why girls are having all the fun in all this, being on the baby side of the equation, it’s because the market is stacked pretty heavily in their favor.

Women often become sugar momies later in life, but are able to be selective due to a flooded market of willing and able male suitors. Photo by Edward Cisneros

“I think that women are also looking to being sugar mommies, but the fact is there aren’t lots of them,” Jessica explained. “The way women are, we usually prefer to be monogamous; we usually prefer to have one partner for a long time. It makes being a sugar mama pretty easy as far as straight males go. There's plenty of them jumping in bed to get hot older women to help them out or even date. There's not such a stigma around that as there is around women doing it. So not only is the pool larger, they also have more options as sugar mommies; they have their pick of whoever they want and then they get off the site because they prefer monogamous, long-term relationships. I'm not saying all of them, but that's why there's not as many.”

Jessica speaks from experience, having worked closely with Seeking Arrangement as well as being a sugar baby herself, and while her experience may not be the standard for every woman looking for a man to provide the lifestyle she aims for, she has had a storied tenure in the lifestyle.

“Yes, I do like when men pay for things for me,” she stated. “Yes, I've been taken on trips and been bought nice things and they help me pay for whatever it is I'm asking for and that's just part of the type of relationships that I'm seeking. I don't really see them as a problem as long as I'm honest about it.”

If you find yourself looking to dip into this lifestyle, Jessica did give five helpful tips for finding success:

1. Check your jealousy at the door

You know what you’re getting yourself into, you know this man has a wife at home and potentially other mistresses. This is not the type of relationship to get into if you’re always catching feelings.

2. He’s not leaving his wife for you

Even if he says he is, and you swear your love was written in the stars — and it may be — he is probably a family man and feels responsible to continue his role as husband and father.

3. Don’t try to contact his wife

If you feel like you’re going to make him leave her for you by telling on him, you’re dead wrong. Be prepared to be the one left behind if you decide to spill your little secret.

4. Recognize what you are getting out of the relationship

Do you like expensive handbags and upscale restaurants? Or maybe it’s the companionship of someone more experienced. Or maybe it’s the rush of getting caught. Either way, you’re getting something out of this arrangement or you wouldn’t be in it.

5. Know your self-worth

Being the other woman can be hard on the self-esteem. You may feel your ego pushed to its limits. However, if you start to feel like your confidence is waning, it may be time to move on.