OKCupid Tips – What NOT to Say in a First Online Dating Message

When it comes on online dating, I’m rooting for the dudes. I would prefer to see them do well than do poorly… and yet so many stick their feet in their mouths with their first message to a promising target.

I would not have thought this to be the case- one of the benefits of online dating is that guys have the time, anonymity, and resources to be suave… or at least to test out various tactics to discover (and use) only the most effective ones. But after making my own happy little profile on OKCupid and watching the messages slide in, I have to say… I’m somewhat dismayed.

Guys, you deserve some action. Really, you do. So let’s go over what NOT to say when reaching out to all those lovely ladies. I’ll provide real examples, of course (with proper protections of anonymity applied). Even if you know better than to make these mistakes, you might find them funny.

…. but first, full disclosure time! I am not here to offer relationship advice. I do not date, nor did I join OKCupid looking to date.

I make it very clear on my OKCupid profile that I’m only on the site to check out the UI, which is fantastic, by the by. So folks who message me may not be the brightest OKCupids bouncing about…. but I still reckon these are common mistakes.

Lame Comments About Images / Appearance


Men, I think, have been conditioned to believe that they can never go wrong when complimenting a woman. This is not always the case, but I’ll go out on a limb and say that offline, such compliments in the pursuit of boy-girl relations are a safe way to go.

Online, things are different. It’s pretty much a given that nobody is going to contact you unless they’re cool with the image(s) you uploaded. So compliments on images are pretty much pointless. They might also come across as a bit creepy. But maybe that’s just me.

Some examples:

Hi there. i like ur pics, it looks like u have a lot of fun

As most photos people upload are of people looking like they have a lot of fun, this could easily be a generic message (more on those in a bit, but in short, generic messages are not the way to go).

Hi, You look great! How’s it going?

Another very generic message. If you’d like to compliment another user on her appearance, I recommend explaining why. Before it was flagged and moderated, for example, my OKCupid profile image had me in a full body goose suit. Perhaps this bachelor could have explained why I looked great in my giant goose costume.

Form Messages

I understand that it takes time and effort to send lots of messages to lots of people on OKCupid, which would be my approach if I were looking for action. It helps to cast a wide net, right?

That said, sending form messages is not the way to go. We live in an age of spam and unwanted form emails. We can spot them a mile away.

Here’s an example:

I’m *****. 25, 6’5″, brown hair, green eyes, fit. live in the ******** in sf. I’m vegan, like to meditate, go to a lot of shows, read a lot. I like surrealist art, I make films, currently editing my psychedelic ********** feature. Can you touch your nose with your tongue? You’re cute and seem cool. We should chill. What’s your week usually like? Can I txt you?

****** here is a catch, to be sure, but his message could be sent out to anyone and still work, hence the inner “FORM MESSAGE” warning in any internet savvy gal is going to go off when she reads this. Another mistake here: describing stuff that is already in his profile.

A better approach? Find something in each user’s profile that you could comment about, and make the first message about that. “I see you’re a vegan, too. What made you decide to give up meat?” is a really easy one Shane here could use, for example. Or “I see you loved [insert book/movie/band/show here]. Have you seen/read/listened to/watched [insert similar book/movie/band/show]?”

Gender Issues

Ok, so maybe guys on online dating sites have had issues in the past with girls who are not girls saying they’re girls. And I can see how that would be somewhat traumatic. And how easy it would be to mislead people. So sure, some guys on OKCupid are a bit shell shocked, which may explain some of my more favorite messages received:

Hi are we a T girl?


OOOOOOO your a guy sorry man I didn’t read into that too well my bad

In all fairness, I may have said something on my profile to the extent of “So far as you should be concerned, I’m a dude.” Just maybe. But for the sake of thoroughness, I would like to recommend that OKCupid users not broach this subject until later in conversations. Not just because it prevents them from initially coming across as paranoid/hilarious, but also because, in all fairness, most transexual women look WAY better than, I would argue, most of the ladies out there. Myself, definitely, included.

Text Speak & Poor Grammar

It should go without saying that proper English has a leg up, at least in initial conversations. Anyone can write poorly or in shorthand, so it is far more impressive to use proper grammar to start with.

Why folks opt to use poor grammar in a first message escapes me- especially when real English rolls out in subsequent messages! Perhaps the English language really is devolving, and not even into lolspeak. Sigh.

While text speak and slang may be a bit of a turnoff, poor grammar is a total death sentence. Consider this example:

First that all great pictures. About Me. I’m 29 years old, nice man, I had been living in San Francisco since 2002. I love to enjoy what this nice city offert us, as a restaurants, bars, clubs, parks, beaches, I’m giants and lakers fun. I also like to do exercises as a run, play soccer in a legue every Sunday. And sometimes basketball. I also like to watch sports . Of course i have my job that i love it, and also i go to school. Tell me more about you.

Note the odd capitalizations and lack thereof, errant spaces, and improper word usages. Alas, though this is a friendly enough message, its well-meaning sender has made himself look to careless to merit a response.

Messages That Look Like Spam

Some examples:

Hi ,
May I know your name please?
I like your profile and would like to know more about you.
I am in ******* for doing my Summer Internship. Basically I am from ******.
Would you like to talk to me as a friend?
You can shoot your questions too.

You might look at this and think that, slight grammar mistakes aside, this is a perfectly fine message. It would be, but for the “Hi ,” which (and this could be just me) is the first thing I notice in a vast majority of spam messages.

Starting any message with “Hi ,” or “Hi, Dear” or any sort of sentence that leaves a space before a comma or that first punctuation mark is a dead giveaway that you’re using a generic message. Even if your email is great, that initial beginning might be enough to sour the potential affections of your mark, as the subconscious thoughts of spam messages that that opening line left may leave an unpleasant feeling in her mind.

Some other small pieces of constructive criticism:

  • Summer Internships do not require capitalization – I only capitalize positions in formal writing or when I’m trying to impart an ironic tone of self importance
  • “You can shoot your questions too” makes no sense; perhaps this sentence would make more sense with an “over” or, better yet, it could be preceded by “I hope you shoot yourself.” which would certainly intrigue some readers and encourage a response.

Invitations to “Check out my profile”

Girls, I am told (I wouldn’t know), are not super big on guys who are only interested in themselves. Unless they are famous/incredibly rich/super gorgeous. In the online dating realm, it’s a safer bet to avoid anything that might hint at self-importance before proving one of the above factors. Even borderline cases are not worth the risk:

Hello. Your profile is full of personal’ty. Message me ba’k after reading my profile. 🙂

In the example above, the OKCupid user does make a friendly acknowledgement of the person he is messaging… but it is generic at best. Giving another user homework (read my profile) is not a good way to start things off.

It might be better to allude to having things in common or to offer a compliment of the target’s taste in books, movies, or music. Such might encourage her to visit your profile out of a curious desire to see what movies/books/music you like.

Pointless Salutations

OKCupid enables users to smile, wink, favorite, and visibly stalk each other, so if you don’t feel like writing a complete message, don’t write one at all. Sending over messages like:

silly Sally!


Hey, I’m ******** 🙂




Ya the government sucks!

Is not enough. I, for example, already know that I’m a silly Sally, I can see your username already, I would have probably messaged or stalked a user if I were interested, and I don’t know quite how to respond to such brief commentary.

As my high school AP art teacher used to say dismissively when we presented her with our various anguish-ridden works of art: “Embellish!”

I suggest you do the same.

Good Hunting!

I hope you have found these real-world demonstrations to be helpful in your online dating exploits. Online dating is awesome, and I imagine that there are lots of perfectly nice folks out there who, unlike myself, are looking for exactly the same thing as you.

So good hunting, and may the odds ever be in your favor.

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