It occurred to me that while I’m in the business of posting public service announcements to the online dating site users of the world — i.e. examples of what definitely not to write in messages to would-be new friends — I should also point out some of the more subtle ways in which attempts at initial flirtation can fall short. The following are a few of the recent OkCupid messages I’ve received that, despite avoiding crude come-ons and functional illiteracy, still didn’t inspire me to reply.
Message: “Though I’m far away I would very much love to hear from you. As you said it’s good to hear from fellow kinksters. I feel like I’m the only one where I am… See if you want to chat maybe after reading my profile. I’d love to hear from you.”
Mistake: Though this user gets points for sharing my interests and having read my profile (I mention welcoming shout-outs from “fellow friendly pervs”) the fact that he lives 1,997 miles away — and that I’m not currently looking for cybersex research partners — means he’d have to blow me out of the interweb water for me to even read his profile.
Message: “just read and enjoyed your profile. definately a fan of spanking, calling naughty, name calling, pinning your wrists down, etc. oh wow. used to be totally into cyber stuff too, though haven’t done it in awhile. hope you’re havin a fun night.”
Mistake: Okay, in my profile I do come right out and say I’m a bi, poly sub, but read more carefully, OKC-goers: under “looking for” I don’t list random hookups. Even if I did, I’d take it as a red flag that you jump right into the a la carte sex menu before even introducing yourself.
Message: “So interesting professional skill you’ve got there, cybersex. I’m still working at it. HA! Hows it going? So I”m curious what your looking for on here since it looks like your married?”
Mistake: Call me a hypocrite — or just a sex writer wary of sex — but this comes on too strong as well. Let’s bond over how adorable Welsh corgi puppies are or something before we come to the mutual understanding that first and foremost what you want is to get into my pants.
Message: “Hi there! How are you this morning? saw your profile and thought i’d say hello. Have you been a member here on okc long? I’ve been on for a few months, but its not working as well i hoped it would. Anyways, i read through your profile and noticed that you are poly.. I am as well.. So i thought i’d look around on here and set up a group of poly friends to get to know. So if you’re interested, or just up for a good chat, send me a message sometime :p hope to hear from you!”
Mistake: There’s nothing particularly striking here — beyond the fact that this user is also poly and lives in my city — but to be frank the deciding factor wasn’t the content of his message, it was his photos. I didn’t find him attractive. Cruel? I’m hoping it’s more like honest.
Message: “I just wanted to drop by and say hi (which it appears I accomplished). I am quite new to the city (moved here from Iowa about 5 months ago) and am always in search of new, awesome people to hang out with. A little about me; I am a fun, energetic, and intelligent human being… While a relationship that was something more then friends would always be welcome I am basically looking for new friends at the time… If I sound like someone you would like to get to know please send me a message back.”
Mistake: While this is a sweet, endearingly vulnerable message — three full paragraphs in its full form — it’s the equivalent of a form letter. How many people did this nice young man send it to? You wouldn’t do it when applying for a job so don’t do it to me, buddy. But, you know, good luck with the friends and stuff.


Bonnie Ruberg is a sex, technology, and video games journalist who contributes regularly to publications like The Economist, Forbes, and The Village Voice. By day she's also a comparative literature PhD student at UC Berkeley, where she studies French, English, gender, sexuality, surrealism and perversion. You can reach her at [her first name and last name, all one big word] AT gmail DOT com.
October 20th, 2009 at 11:43 pm
You know, I study communications for my undergrad, and it’s basically one giant marriage counseling course. Point of the matter, I just got back from a topical class, it was that there are essentially three types of initial communications to potential mates.
1. Flippant 2. Direct 3. Innocuous
and people who essentially use 1 are… the bulk of people who don’t understand what they’re doing. Guys apparently think it’s them being witty or something.
People using 2 sometimes succeed, but they don’t with you, I guess. These are comments that get to the point. “Hi, you seem pretty nice, I like you. Come hang out with me.” Blah blah blah.
3. comments are devoid of smelling like someone is hitting on you. Like “Do you know if I just missed the bus?” to start a conversation.
Studies show that innocuous comments are the most likely to succeed. And from what I think is going on with OkCupid, is that it’s almost impossible to have an innocuous comment. The site, for the most part, is a dating site. So people that message you fall into category 2, even if the message in another circumstance, may seem innocuous.
At least that’s what I can observe from your post.
October 22nd, 2009 at 2:20 pm
I agree with you in a larger sense, that no OKC message can be totally innocuous (though I currently have a clause up in my profile that I’m not looking for new partners at the moment, so I get a lot of “This isn’t hitting on you because you’re not looking for dates right now” messages, a few of which have indeed turned into dates, leading me to believe that the seemingly innocuous really does work on me :), but I definitely still prefer the ones that at least appear that way.
I also wonder about flippant messages. Is that somehow related to the “neg” technique of picking up people? I, for example, dated a boy for a few months whose initial message said, “We’re obviously too much alike to ever actually get along, but I just wanted to tell you how much more I rock at Guitar Hero than you.” That’s probably more cocky than flippant but still, ended up working like gangbusters.
October 23rd, 2009 at 3:36 am
Well, “flippant” how it was described to me were short and often sexual in nature. The “too much alike to ever actually get along.” doesn’t make it innocuous, but perhaps there’s a whole new level of it in it being OKC.
Flippant comments from my understandings are pick ups like “I need a map because I’m lost in your eyes.” or “Do you like fruits? Because I have a banana.” I always thought they were just horrible jokes, but I guess guys really do use them. I did hear “I’d like to get behind you.” from a bar patron while waiting, so I guess it’s more likely than I think…
October 25th, 2009 at 5:26 pm
I personally prefer “Does this smell like chloroform to you?”, but I’m not sure how flippant that would be :).
October 31st, 2009 at 6:19 pm
You’ve made a lot of sense with the ideas you’ve shared. Definitely on target for what my friends and I need to know. We’re making lots of mistakes trying to play at getting it right. We should probably take things more seriously.
November 6th, 2009 at 10:24 am
LOL @ “does this smell like chloroform to you?” Now that’s TOO FUNNY! I do have to say, when I tried online dating I was only successful 1 out of every 15 or 16 ladies I met. Thinking back on it now, I do feel I could of been a bit “flippant” in my “directness” on how I wrote to these women!
In my time, I found pick up lines to not work! What works for me is being observant & attentive; which IS harder to do in online dating! At times, I find myself a “bit” different then the average guy because what turns me on is a woman’s personality! I do enjoy physical beauty, don’t get me wrong, but when the woman has physical beauty & no inner beauty whatsoever, I feel it’s time to move on to the next one! ;-P
November 22nd, 2009 at 5:19 am
i have avoided online dating like the plague – everyone can be whom they want online and most people are less than truthfull. The internet is a good thing and its certainly a paradise for sex freaks who are on the prowl. oh well some of the pick up lines are funny!!