How to Cold Approach a Woman on the Internet

Reading Lauren Hockenson write about being approached by straight men online as a straight female writer in San Francisco for Femsplain reminded me that I’ve long wanted to write an instruction manual for men on how to approach women.

Men are legitimately stuck between a rock and a hard place when it comes to approaching women. I was going to add, who they are sexually interested in. But it’s not just that. Women are on guard in all interactions with men. My heart especially breaks for the men who are not socially savvy, both because I am socially awkward, and because that’s the kind of man I often go for.

The rock part is that the reality for most men is that if they don’t approach women, they lose out on any chance of having sex with them. Sure, some men get approached sometimes. But for the most part the social expectation within heterosexuality is that the man approaches. If he doesn’t, he’s a pussy or a prude. Women are similarly bound. If a woman approaches a man, she’s seen as easy or a slut. Again, there are thankfully many exceptions and society is becoming less stringent but those are the norms.

The hard place part is that if a man approaches a woman in a way she doesn’t like, he is often not only cut off from any chance of being with her, but he can also gain a bad reputation, and even be accused of harassment.

I’ve joked that straight men on the internet make me want to be gay more than anything else. But in reality I think most men are well-intended, but just generally clueless about how to do this right. Which leads them to either not approach, or to approach wrong.

To help the situation, here’s a handy guide for straight men on how to cold approach straight women on the internet. Again, the default is for sex or a date, but really these tips apply no matter what you’re approaching her for.

Understand her situation
Chances are, you’re not the only dude approaching the woman in question. Women who put themselves out there on the internet in any way are absolutely bombarded with messages from men they’ve never met wanting various things from them.

This goes back to the math problem we mentioned above. Men are supposed to approach. Women aren’t. So men approach. But only a small percentage of men and women really put themselves out there to people they’ve never met. Men can only approach the women they know exist and have given them some reason to be interested. That only describes a small percentage of people. And of that percentage, most are men, since women are less willing than most men to be public online in any real way.

So she’s bombarded. And most of the men who reach out to her cold are not socially adept. The men whose primary method of flirting is cold messaging pretty women online do not tend to be the smoothest men on the planet. I love you guys, but it’s true. Smooth men go to bars. They date their friends’ friends. They do online dating, even. But they don’t cold reach out.

Which doesn’t mean you shouldn’t! Chances are if you’re online long enough you’ll run into someone you really want to start a dialog with. You should absolutely try to do that. But you need to understand things from your target’s perspective in order to now blow it.

She’s also bombarded, likely, with actual harassment. Women online constantly have to deal with men sending them rape and death threats for daring to make their opinions public. If you’re a woman and you put pictures of yourself online, your looks are going to be constantly commented on, unbidden.

All this puts her on the defensive. This is why the wrong approach won’t work. It’s not that women are snobby or entitled. It’s that they’re under siege. Women don’t have the bandwidth to give you multiple chances to get it right. Taking a chance on every stranger is impossible, and taking a chance on any stranger isn’t advisable for a woman online.

Provide something of value
That’s why you have to give her a reason to respond. Access to your dick is not a reason to respond. Repeat after me: Dick is abundant and low-value. Your attention and interest in her is not a reason to respond. Attention and interest from random men is abundant and low-value.

Things that are of value:

Relevant information

If she writes about sex and politics *ahem* then a link to an underreported or can’t-miss news story relating to sex work is valuable to her. I’m not saying this will get you a date, but it may get your foot in the door.

Access to useful people

Do you know the editor at a publication she really should be published in? Offer to connect her. This is extremely valuable and is a great carrot for getting her contact information. Offer some information about yourself before asking for her contact details.

Welcome feedback

She doesn’t care if you didn’t like her latest article. She sure as fuck doesn’t want to hear why. This isn’t the playground, and that’s not flirting. It’s being an asshole.

But, if you can correct her facts and provide citations, or help her make her argument more sound, you may have an in if you can do it with extreme humility, politeness, and kindness. She has no shortage of men trying to make themselves feel important by insulting her or her work. But men who appreciate her and want to help make her better are valuable.


If she complains about something, offering to help her in a way that costs you little can be a great ice breaker. For instance if she doesn’t know where to go to get something done, and you do, tell her what you know.


Some women will be insulted if you offer cash or presents as an opener. Others will be intrigued or flattered. It’s a risky bet, but it’s also easy. And it’s more likely to get attention than “Hey.”

A friend of a friend got a date by buying a woman a wine class.

For me, I’ve met at least one friend through my donate button. A donation with a nice note led to me writing him a thank you email. Which led to us talking.

Please note: A compliment from a stranger does not really add value. Certainly not enough to warrant beginning a conversation.

Lose the entitlement
I can’t tell you how many times I’ve gotten a message online that just said, “Hey,” “Hi,” or “What’s up?” I have no shortage of men to talk to. Why in the fuck would I respond to your inane message, stranger on the internet?

Even worse, some strangers will ask for information about me as their opening message. To then make it even more appalling, some of these men will get angry that they’re being ignored.

Men on the internet are incredibly entitled. Don’t be like that. A woman owes you absolutely nothing, ever, unless she agrees to it first. Even if you try literally everything on the list to add value to her life, unless she agreed to do something for you in exchange, she doesn’t owe you a damn thing.

The sooner you get that, the more successful you will be.

I’m not saying these tips will guarantee you success. In fact I’d put your odds of getting a response from a woman on the internet you’ve never met at quite low, regardless of how impeccably you approach her.

But I will say they’ve all worked on me. I have had many friends and lovers who I’ve met online who approached me cold using one of those tactics. And I’m not likely at all to respond to a cold approach that doesn’t use at least one of them.

So go forth and prosper. But keep your expectations in check and leave your entitlement at the door.


  1. Bob Robertson

    Oh no, if I comment here, will it be taken as flirting? :^)

    Seriously, I think it would be helpful if there was some way in American equivalent to the British “I fancy you”. I guess “I like you” comes close.

    Even I’m put off by the quantity of “Oh your pretty! Slobber Slobber” that I see online. Is it time to blame government school again, this time for releasing perpetual emotional adolescents upon the world by the millions?

    The only advice that I’ve ever seen work is, “find someone with whom you share a common interest”. That would go along well with your point about “have something to offer”.

    Thank you for writing this, good advice.

    Peace, may your aim never waver.

  2. Useful advice even for same sex dating, or as you say trying to get something out of someone other than sex (and even if they aren’t a woman).

    Though lots of the dynamics and background are heterosexual specific.

  3. Melinda

    Thank you. Besides linking my favorite blog of all time (the Dickonomics of Tindr) you’ve captured everything their mamas *should* have taught them years ago. If their mamas had been online. Or sentient. In my own experience, no matter how plainly I state my interests and dislikes in an online dating profile, the number of “Hey”s and “How’s your weekend?”s from babies who are way too young or guys who live 500+ miles away never diminishes.
    Please consider publishing this in RoleReboot and other venues.

  4. Jeff Anderson

    Hey Cathy,

    Really good article!! Normally I don’t read blogs but you choose a good topic. Cold calling is a necessary reality we all have to face.
    I also liked your brutal honesty. Sure it’s not pretty but it’s the reality.
    I also like your emphathy and honesty to these problems that bros looking for hoes or Nerds looking for anything face everyday.


  5. Mark

    The best way to meet women is in person as you stated. If you’re not smooth, you can improve with experience. If a guy tells himself he’s awkward and doomed to always be awkward, that’s a limiting belief. Guys need to face their fears. It builds character. And ultimately character is the most attractive quality you can have.

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