I’ve been writing about online dating for a long time now, and I always advise new daters to be honest with who they are and what they’re looking for. But sometimes, daters are too honest. When you’re approaching someone online for the first time, you want to be nice and complimentary without being fawning, and you want to put your own preferences out there without being terrifyingly weird or creepy. This message, sent to a lady on OkCupid, does all of those things wrong:
Hello sexy. I’m a nice guy but I have a small penis. Would you make fun of it and have to cheat on me?
Calling a stranger “sexy” on first contact is generally a guaranteed no-responder. Discussing your tiny penis and seguing into your cuckolding fetish (or not-so-deeply resentment issues)? It’s an impressive feat in two sentences, but not a good idea if you actually want your small penis to ever get touched.
This next online dater makes a similar mistake:
You look very beautiful and your profile fits the kinda people I want to meet, I’m a bit of a sex addict and can’t function without it lol, I know is a bit brutal but that’s the truth, I try to be as honest as possible , pls just say hi and we can chat, you don’t have to comit to anything until you decide if, I will send you my pics no problem.
A lot of things are “the truth.” It is the truth that I drool all over my pillow whenever I nap and that sometimes I fart so loudly in my sleep that I wake myself up. None of those things needs to go in my online dating profile, though, or in any sort of communiqué to a potential suitor. You are choosing what you put in your dating profile. Don’t choose things like “sex addiction.” Or “lol.”
Also: Don't send creepy messages that you know are creepy and then justify it by saying you're just "straight-forward." You're not straight-forward, you're just gross:
Although thanks for the permission, I suppose, to decline your creepy advances?
While you should definitely be complimentary to a person you’re trying to date, it’s usually best to mention something about their listed hobbies or preferences rather than their physical appearance. She knows you find her attractive – otherwise you wouldn’t be messaging her. And the appearance-based comments can come off as creepy. Especially when you lay them on thick, like this next guy:
First off you are absolutely beautiful!! I was stunned as I went through your pictures. Beautiful red hair is amazing!! I am kind of looking for something right now unconventional but I felt I shouldn’t hit you up about it. However I feel like I should reach out. Check out my profile, if your open, let me know? I actually am just looking for a masturbation partner at this point in time personally. If for some reason you like masturbating and would want someone to do it with that would be rad otherwise I wish you all the best. I just am so turned on by your hot body and thought of you potentially being natural with lots of red hair is oh so hot!!
Then again, if you’re using OkCupid to troll for masturbation partners, a few comments about a woman’s appearance are probably not what tips the message into the creep zone.
Excessive compliments, though, are still better than flat-out insults. This next guy shows us how to make sure a woman definitely does not respond to your message:
let me count the ways how you are setting yourself up for failure lol this is funny to me, but seriously i want to at least give you constructive criticism from a male point of view. maybe it’ll help you find whatever you’re looking for, or maybe it will help him find you ;)
your headline sucks
your profile picture isn’t the best, compared to the other pictures on your profile, idk maybe sepia tone or whatever it’s called isn’t flattering to your skin tone. just saying.
Plenty of people suck at online dating, and plenty of their profiles and messages are awful – this column would not exist without those poor souls. But there’s no need to take five minutes out of your day to go out of your way to tell a person, without solicitation, exactly how their profile is imperfect. That actually makes you kind of a jerk who is “setting yourself up for failure lol this is funny to me.”
And no, passive-aggressive smilies do not make bouts of drive-by “honesty” any more acceptable.
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 Cara Vandermey
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