Confessions of a Craigslist sugarbaby

Craigslist w4m: I wonder what will happen

Female seeks generous older man. I’m a 23-year-old woman, I just graduated and I need help with my bills. Contact me if you want to engage in a mutually beneficial on-going relationship.

22-year-old Sarah* lied to about her age to enhance her craigslist request. She had been wallowing in a sinkhole of debt, the result of her increasing intravenous drug use. We are sitting in a cheesy, collegial pub. She seems exuberant; this novel and fleeting capitalization of her youth and beauty is shoring up dividends.The middle-class, University drop-out toyed briefly with the idea of full-fledged prostitution, but didn’t want to have sex with “gross, old, pock-marked men”. So she put an ad on craigslist looking for a sugar daddy.

She received 30 replies from different men.

“You could tell a few were just regular guys who would allot a few hundred to have a girl around some of the time. You had a few wealthy CEO’s – you can tell the scale of wealth when you start talking to them. I could tell based on the content, structure and tone of their message, obviously some will come across as more cultivated and settled. They’re a little bit more subtle and low key about it – like, ‘I’ve done this kind of thing before, I’ve helped a girl through school’ – I wanted to be with a man who had familiarized himself with the routine because it would make me feel more comfortable, because I had no idea what I was doing.”

She narrowed it down to two prospects. One, an oil executive from the States, was an anti-intellectual business mogul that was into Harrison Ford movies and Tom Clancy novels. She quickly ruled him out. The other was a balding, married, pot-belled CEO with erectile dysfunction and a self-admitted “extremely small penis”. He had money to burn and experience being a sugar daddy. She chose him because he appeared to be fascinated with her mind.

“I know my niche. I’m never going to be the hottest sugar baby out there, but I’m reasonably intelligent and I can hold a pretty challenging conversation. I’m a good companion. I’m a pretty good pop psychologist and I have a pretty good theory of mind, I pride myself in my ability to make other people feel comfortable even when there might not be any sort of commonality. So if he can appreciate my intellect, I can sort of exaggerate that angle and make it as mutually bearable as possible.”

He sends her a grand each month for rent, in addition to spending money when she requests ($500 a pop) and a new computer. He recently just gifted her a $500 Burberry scarf.

“When he buys me frivolous shit like this I just think I could have spent on my credit card debt. I’d rather have the cash. Whats a 22-year-old girl gonna do wearing designer shit anyway? I don’t need it.”

He has not requested sex, although she would not rule it out. They go out on ‘dates’, to dinner and musical theatre shows. His wife, an older executive, is vaguely aware of the arrangement but turns a blind eye, so long as he doesn’t embarrass her, publicly.

Sarah is reflective about the arrangement. She relies on him for her “bread and butter”, but resents him as a repulsive, insecure man.

“You know when a guy is trying to get with you, and just because he’s trying to qualify himself to you, you just feel this revulsion? You just know what he’s after and you know how transactional it is and you just can’t help but see him in the starkest light.”

She did her research and learned from other sugar babies that it is best to leave your problems at home, creating a fun veneer of wistful reckless abandon. They don’t want to feel like they’re exploiting a charity case. They want a fantasy figure that gets them away from their wives and children, a muse that makes them feel invigorated and effectual.

“Its like that whole ‘manic pixie dream girl’ term, this trope in pop culture – like for example, Natalie Portman’s role in Garden State. Like Zoe Deschanel’s character in anything. They’re underexplored female protagonists that their life isn’t very examined but they act as a sort of mirror or therapist for the male love interest. So his life gets explored and he’s really the protagonist and he has all the agency and she’s just there to help him explore his life, this flitting and capricious fantastical character who does shit like dancing in the rain, takes road trips, she’s spontaneous, there’s nothing holding her down, she has no real life concerns. Essentially you are acting like that sort of archetype, especially in a sugar baby role.”

Her sugar daddy has had two previous sugar babies, spanning over a decade. For their first date they went to a Greek restaurant and chatted about his life. Occasionally, he will grope her or make out with her.

She does have a real boyfriend, who is OK with the situation thus far, largely because he has directly benefited off of it. But she still has doubts. Her sugar daddy cannot learn about her real boyfriend or her drug habit; it would shatter the carefully constructed illusion.

“I want to find someone who can deal with that or is willing to support me. But most of the guys I’m interested in also engage in the social periphery. They’re not going to be 9-5 successful guys. I still want to have space for an authentic relationship in my life. I don’t want to be single and have my sole companion be some lonely old man who I at best, pity. Outside of that consideration, I don’t think it’s affected me in any major way.”


Tiffy Thompson is a writer and illustrator for the Spectator Tribune.  Follow her on Twitter at @tiffyjthompson.

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