“Oh why must I feel this way? Hey, must be the money!”

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At any given moment, in any given city, some guy is texting these words to a woman.

Let me fly you out for the weekend doe

He might not be an athlete. He might not be a rapper. He might not even be a creepy, old man who wants to buy you a new chest. He’s young, he has money, and for reasons that may or may not be known to you, he wants to upgrade your lifestyle.  He is the Generation-Y sugar daddy.


At first glance, I never would have thought that I’ve ever met of this type of dude. I, like many, have a really stereotypical idea of what exactly a sugar daddy is. He owns a business. He’s old. He uses an oxygen tank. He’s old. He wears silk robes and says things like, “Come to daddy.” Plus, he’s old.

Then, a year ago, I went to a housewarming party for a friend from college. His family owned a large franchise of restaurants, and he was only 27.  I’ve known him for almost a decade, and I didn’t think he was paying for flights.  He showed me conversations he had with women that revolved around fancy restaurants and amazing spas he would tell them about.

“Is he gay,” I wondered?

He would send women pictures of hotels he was staying in and bags he liked (at this point I definitely thought he was gay). He’d ask their opinion on the cars he wanted to buy and hint at vacations he wanted to go on. Within a week or two, he was offering to fly them out to exotic places, saying he wanted to “take care” of them.

What? Take care of her? Is this normal? Is this a thing that’s actually happening with people my age? Young, wealthy guys of our own generation actually want to settle down and wife-up a woman? Nah son, I am in the wrong generation. I don’t even take girls out to restaurants with more than two $$ on Yelp. How am I supposed to keep up?

Plus, it had been two weeks. Why a man would want to fly a girl out to any city after two weeks completely bewildered me. I wanted to ask the people who I thought could really help me solve this, so naturally, I asked my female friends.

The immediate consensus was yes, this is happening in our generation. Yes, men are out there financing women and their lives. And yes, it’s because they want to get laid. That’s it – nothing more, nothing less.

However, that didn’t sit right with me, either.  I’ll be the first to admit that men will do a lot for a woman when there’s the potential to have sex with her. However, “a lot” usually classifies as “driving a little far a little late.”  The extent that these men go for a little nookie involves traveling, dinner and some presents along the way – all things that seem less along the lines of “you are my booty call” and more like “you are my girlfriend.”

After more discussion with my friends about these sugar daddy characters, we still couldn’t reach a final conclusion as to what’s in it for these men other than sex. We thought maybe it’s because a lot of these guys are lame and have to buy a woman’s attention, or maybe it’s because some men don’t have strong personalities and money is their way to cover up that flaw. Finally we thought, well, “it ain’t trickin’ if you got it.”

The Gen-Y sugar daddy is a different breed from the sugar daddies of the past. With way too much money at a young age, these guys are willing to take care of women and essentially “court them” with plane tickets, $200 dinner dates, expensive shoes and clothes, and VIP treatment at hotels and clubs, all in return for a woman giving them the “girlfriend” experience. Ya know, why not? All these guys are missing is a Mrs.

Syed Mikhail Hussain is fan of all things NYC and Hip Hop. Winner of the sperm race back in ’89. He does a weekly basketball podcast. Follow him on Facebook, Instagram or Twitter at @swishthis.