6 Messages Not to Send When Online Dating


I’ve been on 100 first dates. That’s not an exaggeration–I actually sat down and counted every painful, awkward encounter one time. I got these dates in a variety of different ways, but the majority of them were derived from the four online dating sites I frequented over the course of about three years of perpetual singleness.

So, if you’ve used your powers of deduction, that means I’ve received A LOT of dating site messages from dudes. And considering the fact that there were 100 messages I responded to, it is entirely impossible to estimate just how many messages I got that I didn’t.

Hundreds? Thousands? Seriously, the world may never know.

As I said, when I got bad messages, I never wrote the message sender back, which I realize now was a mistake. How can you ever improve on something if you don’t know what you’re doing wrong?

I’m sure many BroBible readers are on dating sites, and I’m sure some of you are merely getting crickets in response. Well, read on to see if you’re committing any of the following no-nos when crafting your communiqués.

Message mistake 1: Being too familiar

You may think you’re being complimentary, but if you start your messages with “Hey sexy!” or the like, your rate of return will be less than you hoped.

Why? Because you’re a stranger, that’s why. You don’t know the woman yet, so you shouldn’t be using pet names. It’s creepy. Save “baby,” “cutie,” “sweetheart” and all other nicknames for the point at which you’re also calling her “girlfriend.”

Message mistake 2: Sending form letters

If you’re copying and pasting the message you’ve crafted so you can blast it out to as many women as possible, you’ve already messed up. It is always SO OBVIOUS that a guy has done that, and it’s extremely unattractive.

Women want to feel like a special snowflake that you’ve picked out from the bunch, not like a part of an assembly line. You have to send individualized messages. Read her profile and pick out particular things to chat about. I know it takes more time, but you’ll have greater success in the end.

Message mistake 3: Not hitting spellcheck

Whne ur mesage looks lik this, you seem like an idiot, and nobody wants that.

Here’s a rule of thumb: There will always be women who are bothered by misspellings and poor grammar, and there will always be women who don’t care what you type like. If you send edited messages, you’ll be able to elicit responses from both groups; the opposite is not true. Put the odds in your favor by doing a quick once-over before hitting send.

Message mistake 4: Writing too much

No one should ever have to say TL;DR in response to a dating site message. Save the prose for when you write the Great American Novel and put your romantic designs in more manageable chunks.

Remember, online dating is like fishing–you only need a little bit of bait to get a bite.

Message mistake 5: Not writing enough


That is not an acceptable message to send to a woman you’re trying to woo. You have to write at least one complete sentence if you want to have any hope of getting a response.

Between this and the previous bullet point, I know it probably feels a bit damned-if-you-do, damned-if-you-don’t right now, but the point is that it’s all about striking a balance. Find the happy medium and you’ll do just fine.

Message mistake 6: Being fucking gross/bizarre


That is an actual message I received from a man on a dating site. WTF.

I won’t even pretend to understand the mental gymnastics this man had to perform in order to make himself believe that this was in any way appropriate. This is the kind of shit that makes women think you want to turn their bones into wind chimes.

Keep your messages devoid of any foul terms (like “queef”… YUCK). If you wouldn’t say it to her face at a bar, don’t say it to her in an email online.

With these rules, you’ll be sure to boost the likelihood of getting a response from that cute girl you’re eyeing on OkCupid. Happy dating!