Online Dating and Fellating: Online Dating Nightmares

If Sexts and Subtext is where I try solve your texting issues and Ask a Pro is where I verbally fellate myself for 800 words while pretending to give advice, then this is for you. “Online Dating and Fellating” is a place for you, dear reader, to share with the world your worst, best, most horrific, and most hilarious online dating interactions. Think online dating’s something you want try? You might think twice after reading these.

Head Pro,

I thought it was a funny coincidence that 3 days after I decide to give OkCupid a try you put out a Propinion piece on online dating. When I read your request for horror stories I just had to send this one in.

He sent me his first message this past Tuesday, which I ignored, so he followed up yesterday. I would have ignored the second one as well but I was afraid he'd never stop… Sorry, I deleted his first message but it was basically the same as his follow up. I blocked him after my last reply, I don't need to waste my time on duds. I think I may have stumbled upon the “nicest” (most nauseating) nice guy…ever.

I’ve never tried OkCupid myself, but doesn’t it work like any other site in that it has pictures and a description in your profile? If so, how does he think you haven’t yet made up your mind on his appearance and at least passed some judgement on his personality? No one looks at an online dating profile and thinks “hmm, he’s kind of ugly, but I bet he’s cuter in person.” As a rule, people are only as attractive as their ugliest picture.

I also like how by attempting to remove any sense of pretense from the date, he assumes you’ll forget that he’s messaging you through a website designed and built for people looking to exchange polluted bodily fluids with one anothers. Guys try to pull this shit all the time, and it makes me weep for the male gender. “I’m so nice that I just want to buy you dinner, nothing more! Can we have sex now?” If you’re on OkCupid, the concept of “something more” need neither be implicit nor explicit – the fact that you’re on OkCupid makes “something more” kind of the point. If you just wanted friends, join or whatever it is losers do. They need to build in a feature so that when people like him send a message like that, their phone explodes.

Head Pro,

I recently started a profile. I got this gem of a message (short novel?) last weekend. Needless to say I blocked the guy. He thinks he can support me with $350-450/month? Haha.

This is usually more screenshots than we’re good for around here, but this is something that had to be shared with the world. I wish you’d given me a little more background as to what’s going on here. Is this is first message? Was it unsolicited. Because if this was out of the blue and he’s assuming that a) he wants a relationship with you and b) you’d be willing to move, then wow. A few observations:

– What’s with the money thing? $10k per month is about $120k per year, and if taxes take 1/3 that leaves him with $80k. That, by anyone’s standards, is a respectable living, but maybe don’t lead with that. It’s not going to impress anyone unless you can tack another zero to the end of that figure.

– He likes younger women, but rather than for creepy reasons it’s because your health insurance is cheaper? Actually I take that back, that’s a way creepier reason.

– Mammograms. “I need to let this chick know that I’m ‘bout it’ and know about the difficulties of having women parts.”

– “Slipping”. What’s up with this guy’s job and his variable income? Is he a drug dealer? Does he perform back alley abortions and/or mammograms?

This is the kind of guy who has zero social intelligence and figures that online dating means it’s ok for him to intellectualize the dating process (hence all the talk of money, because girls like money). Usually, this type of guy’s profile says something to the effect of “I’m just a man who knows what he wants and isn’t afraid to ask for it. I’m very straightforward and am tired of playing games, and I want a woman who feels the same. If you’re not looking for a true gentleman who’s willing to treat you right and support you, then you’re just like every other vapid bitch on [insert site name here]. Don’t waste my time and I won’t waste yours.”

Translation: “If you burn my dinner again, you’re going back to the hole for a week.”

Send your online dating nightmares to


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