Relationship Advice - Men

Get Everything For Free: What is it Like Dating a Sugar-Mama?

You’re a broke college student and after weeks of eating ramen for breakfast and linner (that’s lunch and dinner, because like I said your broke), you’ve decided to take your destiny into your own hands. You don’t have the time for a second job with school work and your first job. So what do you do? Well, maybe you need to go on a bit of a safari and see if you can’t find yourself a cougar (relax I am not condoning or promoting this type of behavior…;this is for comedy’s sake people, also if you’re not familiar with what a cougar is, it’s usually a well-off woman in her late thirties early 40’s and beyond). But are you man enough to have everything paid for you and be wine and dined? Let’s see what it’s like to date a sugarmama.

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stiflers mom has got it going on

Cougar and cub seen in their natural environment, the sound proof basement.


Of course, when attempting something new, you need to be down with the lingo in case you come across as uncouth. First off, a sugar-mama is usually a cougar, but not all sugar-mamas are necessarily cougars, I will not be illustrating said distinction with a Venn diagram because honestly I suck at math and all math related items. Second, a cougar is generally a woman in her late thirties all the way up to her late 40s and are usually quite dominant and in great shape (thus the association with the predatory feline).

The young man (the prey) is known as a cub, due to his age. Now, some cougars get a kick from being called such, some will punch you straight in the scrotum at its utterance, you will have to discern this with trial and error. Finally, a sugar-mama is a woman that is generally a well off professional and will take a young mate, either as a show of dominance, for their sexual stamina or both. They will also pay for dates, buy gifts and try to seduce the young man. Often, it’s a complete reversal of gender stereotypes. The age gap is usually significant between cougar/sugar-mama and cub, the cougar often being twice the cubs age.

Is it Easy?

american pie deux

You’re mine now little boy…..


What are you thick? Is there anything on the face of this blue planet that is easy? Even the song “Easy Like Sunday Morning” is full of it. What is easy about the day before of the worst day of the week, forcing you to clamor in preparation. Sure, you can sleep in for a bit more than normal, and you can idly watch cartoons like a ten-year-old, but eventually your brain (the a$$hole) will say…;”Monday is coming” like a grey matter Stark. Likewise, although the idea of an attractive, sexually experienced woman that has finally overcome her inhibitions and is relishing in her sexuality while having no qualms about wining and dining a young dude that can keep up with her sexual appetites sounds awesome, it comes with caveats. Or rather, it also comes with baggage.

We are defined by our experiences and no matter how you spin it an older individual will have many more than a younger person. If you’re dating a younger woman (say a college classmate) they’ll have more or less the same experiences as you (relationship wise): first crush, the big adolescent relationship that ended in expletives and fire and the first “adult” relationship. An older person could potentially add to that list: a divorce, an unloving spouse, children maybe even a cheating partner or two. Beyond the relationship stuff, your sugar-mama will most definitely have work related anxiety (like I mentioned above they’re well off, and when you’re well off that means that you worked hard for it and still work hard for it).

The Taboo

demi moore el cougre

Demi Moore likes her men like priests like their alter boys……young.


As I mentioned in the first paragraph of my article, the older woman/younger guy relationship paradigm reverses gender stereotypes. The reason gender stereotypes still exist is because the majority of people abide by them and anything different makes them go on full “moral panic” mode. You can expect while in the throes of your non-conventional love/relationship/sexy agreement to get dirty looks, talked about in hushed tones and condemned by family and friends (notice I said friends, because your bros will probably ceaselessly high-five you for being in a relationship with an uber hot Milf that pays for everything).

If you are already dealing with a certain level of social anxiety, then dating an older woman might break you down into a sniveling pile of man-child. If that is a fair trade-off for you, free food in exchange for a complete mental breakdown, go nuts who am I to judge (well at least to your face).


me and mariah

Mariah and Nick Cannon, living out every 90s boy’s dream.


The great thing about dating an uninhibited and open minded woman is that the lines of communication are wide open. She will tell you exactly what she wants and where and when she wants it. If she’s feeling frisky, she’ll let you know, and if she does crossfit she might throw you over her shoulder, take you upstairs and ravish you with limited to no effort on your behalf.

This is double edged sword because as a snot nosed cub you might find that this level of communication is disquieting at best and annoying at worse. You are in a relationship, and no matter how little it resembles a traditional relationship, mutual respect is still expected. You need to hear what your partner has to say and take it into consideration.

No Commitment


Madonna’s barely legal bae.


If you’re into non-commitment and shy away from any semblance of responsibility, then you might have found your silver lining in a cougar cloud. This is especially true if the woman’s only motivation is sexual, they will most likely prefer the “wham bam thank ya ma’am” approach to dating opposed to the “wham..dinner and a movie…;.dinner and a show…;six weeks later…;bam…;.lets cuddle mam” approach.

For someone young, dumb and full of…;ehem…;fun, this can be surprisingly refreshing. Add on top of that, the woman will make all the executive decisions, and you have a winning combination…;.maybe?

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So, have you dated an older woman that paid for everything? What was your experience like? Please kiss-and-tell and let us know in the comment section below!