Some Creepy Online Dating Messages Are Better Than Others

Sleazy messages are de rigueur on internet dating sites. At least sometimes they're creative.

The sexytime message is an internet dating standard. Any woman (and many men) who have tried their hand at online dating have gotten some version of “I’d like to put it in your [sic] now” in their inbox — although usually with more explicit language and less fortunate spelling.

There’s nothing wrong with using the internet to find sex, and the world is a better place when more of us are getting laid, so get it girl (and boy). The handy thing about the internet is that folks can be upfront about what they’re looking for — the people who just want to bang can say that outright, and the people who are looking for something more serious can specify that they want dinner first. Everyone wins, right?

Unfortunately, no. Some people are not content to peruse the profiles of women who are similarly up for casual sex. Instead, they shoot notes from their boners off in all directions, often to those who have zero interest in using Plenty of Fish for catch-and-release playtime. It’s unclear what these people are trying to accomplish, since I can’t imagine their porny, often physically improbable sexual suggestions actually get other people going. For example, this OkCupid request:

I want you to smack me in the wiener with one tittie

It that some woman’s fetish somewhere? Probably. Must she have relatively large and flexible breasts to make that work? Yes. But the odds that the woman you just messed on has a slapping--a-wiener-with-her-titty fetish are slim. And even if she did harbor such an interesting and potentially painful desire, you probably disqualified yourself by using the term “wiener.”

But it’s not just wieners and titties that capture the sexytimes dudes’ interest. They also want to please you:

i want to tickle your clit with my big manly mustache

I…. think you’re doing it wrong. Read this, come back later. And shave that mustache, it makes you look like a creepy uncle. At least he doesn't bring up your ex, though, like this guy on OkCupid.

Smiley indeed.

Predictably, the guys who are All About Anal are not only less polite than the pussy-eaters, but also less, um, uptight about spelling, grammar, punctuation and socially-acceptable behavior:

And then there are the BDSM fetishists. Again, seriously, do whatever gets you going, but maybe save it for the third date instead of sending a random person on a full paragraph detailing your kinky endeavors and desires:

Ball gags… hot. Something about a member of the opposite sex being unable to speak properly and drooling like a baby really turns me on. Something about that round piece of rubber in her mouth, held in place with straps… I can’t quite explain the attraction. I guess it has to do with control. I put it in her mouth, I clip the straps, I decide when to take it out. During sex I will often threaten to put it in (ball gag), if she will not keep perfectly silent. This is hard to do when you’re being fucked. I will then put it in and remove it upon completing another task, such as keeping hands above head. Last time I used one, it was amusing to me to dangle it above her mouth — letting it go in, then taking it out a couple times over, before putting it in fully. Also it is fun when a sub fakes to not want it to go in, to play resist, then I plug her nose until she opens her mouth.

Even if you’re into that sort of thing, I can’t imagine this message would elicit a response. Rule 1 of dating: Don't tell a prospective partner details about the last chick you banged, ball gag or not.

But every once in a while, a wildly inappropriate sexytime message strikes exactly the right tone. Like this one:


(Not correct, but if any unsolicited sex message will get a lady to spread, it’s this one).


If you've got your own online dating horror stories, drop them below, or submit them anonymously.

The A(n)nals of Online Dating is a weekly column about How We Date Now, from the proprietor of the website of the same name, showing off the best of the worst internet dating has to offer.

Illustration by Leslie Wood

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