Why asking guys out is awesome

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While there are lots of reasons for women to ask men out more often, the one I’ve been thinking about most often lately is that it can help us learn to cope with rejection.

I have a theory that one of the reasons why women don’t ask for what we want – whether it’s a promotion, a discount, a favor, or a loan – is that we’re more likely than men to be paralyzed by the risk of rejection. Boys grow up asking girls out – and most of them get rejected, at least some of the time. By learning in middle and high school that a rejection isn’t the end of the world, boys see that they can just brush it off and move on. Nothing ventured, nothing gained.

Nothing Ventured, Nothing Gained - TechStars NYC Demo Day

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Girls, however, have conventionally been acculturated NOT to ask, whether it’s for a boy to kiss them or for seconds at dinner. We’re trained to wait for someone to offer. The problem is that no one’s going to offer you what you really deserve. You need to ask for it.

So here’s my proposal – let’s all start asking men out on dates more often. Let’s do it earlier, when we’re younger. Let’s do it, and learn what it feels like to be told “no”. Let’s learn that rejection is really no big deal. And then let’s teach girls that it’s okay to ask for what they want. Because they deserve it.


What do women want from online dating?

Hot-ass red shoes

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It’s pretty commonly accepted at this point that when it comes to dating, men and women are different. We have different priorities, different criteria, and above all, different concerns.

A man might be afraid that the woman he meets online turns out to be ten years older and twenty pounds heavier than her photo. Women are afraid of violence, stalkers, or worse.

That’s why I bang my head on my desk (or the bar) every time I read a male app developer talking about how women will love his app because it’s purple.

Honey, if that’s all it took, Nordstrom would be full of Barney the Dinosaur purses.

Online dating sites and apps succeed or fail on whether or not women use them. So what do women want from a dating site or app? Here’s what my anecdata holds, and what app developers can learn from it.


Women tend to be more cautious about how exposed they are than men. When the excrement hit the air conditioning over the Girls Around Me app, the women I knew split into two distinct camps – those who were younger, more jaded about online privacy, and less worried about what potential stalkers would do with this information; and those who make a habit of periodically locking down their Facebook privacy settings as a matter of digital hygiene. The lesson for women is that any app that encourages you to “check in” probably uses an API (application programming interface) that allows developers of other apps to display that information in whatever way they see fit.

Takeaway: Let women control who can view their profile information, including photos, no matter how innocuous that information may seem to men.


A friend of mine called it the “Preparation H problem” – no one is going to “Like” the Preparation H page on Facebook because they don’t want their friends to know they have hemorrhoids. Similarly, no one – especially women – wants their friends and family to know that they’re trolling for tail on the internet.

Takeaway: Don’t force users to log in to your app using Facebook, even if you promise not to post to their Facebook walls.


Craigslist is the shortbus of online dating. That’s because there’s no quality control, no requirements, and no guidance on what daters should include based on best practices and research. Women spend more than 50% longer than men reading profiles, yet most of the “m4w” ads on Craigslist lack basic information. The more data we have, the more comfortable we are – and there are already too many horror stories about women being harmed by their online suitors.

Takeaway: Encourage all users, but especially men, to fill out their profiles thoroughly with completion bars and percentages or “badges” or other gamification tools.

Should women have all the control in online dating?

Necklace that reads "Pussy Power"

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A new dating site in South Africa has launched with the express goal of putting women in the drivers’ seat. AdoptHim (does anyone else get a whiff of incest off the name?) claims to go beyond letting women block stalkers.

A man can’t see a woman’s profile or contact her until she adds him to a “whitelist” of approved members, encouraging greater profile completion by the men on the site. Men can also send virtual gifts (paid for with actual currency, of course) to show interest.

Back in the days of Spring Street Networks, I appreciated being able to have a profile that was only visible to members I contacted first. I haven’t found an existing online personals site with this feature, so maybe the AdoptHim guys are on to something.

In any event, get a new name. I can’t help but think the site is for male adult babies.

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