Girl Talk: I Was A Sugar Baby

He will be just like Richard Gere in “Pretty Woman,” I thought. He will be tall, handsome, dreadfully rich, with salt and pepper hair, and an insatiable desire to buy me shoes. He’ll probably be a complete gentleman. Have a reservation at some super swank restaurant. He’ll think I’m captivating over champagne and oysters. He’ll love that I’m the stereotypical starving artist. By the end of the night he’ll be so head-over-heels that he’ll offer to pay off my student loans and take me to Paris. Maybe after a month he’ll want to give me a head-spinningly generous allowance and buy me an apartment in the Village. You know, just to keep things easy and comfortable for me so I can have more time to go on auditions. And of course, he doesn’t even expect me to have sex with him.

This, of course, is what I pictured my sugar-baby misadventure to be like.

One ridiculous, outrageous flaw in my personality is that I think I am invincible. I think I can do anything. You know that stupid saying, “Why shoot for the moon when you can land among the stars?” Well, I go past stars. I go to other galaxies. Other dimensions. I almost never see the downside to a situation, because in my mind, I will always succeed. Which is why, when I’m wrong … I am really wrong.

A friend and I were talking about our money problems. Fantasizing about quitting our lame jobs. Brewing up schemes to get rich quick, mostly involving movie-worthy bank heists or finding buried treasure. At the end of this conversation, my friend said, “We just need a hot, middle-aged Sugar Daddy.”

That’s when it hit me. I do. I definitely, totally, completely need a Sugar Daddy.

Believe me. Deep down, I must have known that this was probably a disaster waiting to happen. But I was in invincible mode, hoping for the best. That, and I love a good s**t-show. I would rather things go insanely good or monumentally bad. Mediocre is not my style. Mediocre doesn’t make for the best story.

I mean, why not try? Older men have been benefactors to young aspiring women since forever. It’s an old, played-out story because it’s been happening since the beginning of time. Older, rich man falls for young, beautiful, talented, not-wealthy girl. Man showers said girl with expensive gifts. Not-wealthy girl becomes less not-wealthy. Man and Girl are blissfully happy in their mutually beneficial relationship for years. Right?

I went online and began researching Sugar Daddy websites. I couldn’t decide which was the least gross, so I ended up joining four. I set about doing a disgusting amount of internet e-flirting, wading through profiles of a lot of disgusting old men, looking for one I might have something in common with.

And then I saw Jack.

According to Jack’s profile, he was pushing 40 and owned a consulting firm. His profile listed his yearly income at right around $500,000 a year and his net worth between $5 and 10 million dollars. From his pictures, it seemed like he was 5’10, blue eyed, with an average body-type. Not too bad actually. Not Richard Gere, but cute smile. Jack claimed to “live a fast-paced, exciting and luxe life” and be “looking for a sugarbaby to share the fruits of success with.” Oh, and Jack’s monthly budget for his sugar-baby was $5,000 to $10,000. I thought about what I could do with all that money every month. I messaged him instantly.

Cut to the date.

Meet me at the Soho Grand. There’s a bar on the second floor. See you at eight. — J

I’m wearing my red dress (aka, my sexy dress). I have heels on. I’m leaning casually against the bar drinking a dirty vodka martini, half looking around in anticipation and half trying to pretend like I wasn’t. Nervous. This is weird. What am I doing? I thought. No, it’s not weird. You’re just having an adventure. Think of this as an adventure. This could be fun. Tap on the shoulder. Turn around and … Oh. My. God. No.

Jack looks nothing like his pictures. Jack looks like he’s pushing 50. Jack is wearing an ‘80s power suit that is obviously too small for him. Buttons are about to pop on his red paisley shirt. Jack is easily tipping the scales at 300 lbs. Jack is balding. Jack smells like whiskey.

After trying to hide my initial shock, and awkwardly greeting each other, Jack decides that it’s too crowded in the bar and asks if they have something more private.

Eeeeep! I feel a s**t-show coming on, I thought.

We end up in some posh back room with our own waitress. Before I know it, we have a bottle of expensive wine, an entire plate of assorted meats and cheeses, and Jack is trying to get me to feed him while making loud repulsive jokes.

Either I am a really great actress, or he is just completely oblivious to my disgust. He goes on and on ad nauseum about how much money he makes and how many cars he has. He tells me that he would love to take me on trips and take me shopping. He would also love to give me a monthly allowance and buy me jewelry. Oh, and of course he’s selling me the moon while talking with food in his mouth and dripping wine down the front of his shirt.

Now, I know these are all things that I said I wanted when I was first fantasizing about being a Sugar Baby. But all of a sudden, I realize how gross this exchange feels in actuality—the giving of affection for the promise of material goods. The idea of this huge, sweaty man trying to latch a diamond bracelet on my wrist with his enormous sausage fingers was beyond repulsive. The idea of anyone I didn’t care for, and feel attracted to, showering me with gifts all of a sudden feels off-kilter.

Then, as we all have been expecting, Jack lets the other shoe drop.

Oh, and did I mention? I’m way into fantasy role-playing and feet. How would you like Daddy to buy you some costumes? Hmmmmmmm?

He licks his lips and moves in like he’s about to grope my tits.

I jump up, make a lame excuse to leave, and start putting on my coat. He tries to get me to stay, and when his attempt fails he says: “At least let me buy you a cab home.” Then, he slips a wad of money in my hand.

I don’t look at the money. I’m too much in a hurry to get out of the room. I say thank you and put it in my pocket and practically run out of the joint. I just want to be inside of a cab as soon as possible. I want to be home, in my apartment, no longer fretting about how small it is but just happy to know that it is mine.

Once in the cab, I pull out the money from my pocket. I look down. And there it is … five hundred dollars.


No … Oh?

Hell yes.

Rent is due and mama wants a new pair of shoes. Just like that, the date didn’t seem so bad anymore.

And it does make a pretty good story.