Why is “stalking” a woman bad in the first place? Because the stalker might get so obsessed that they get violent with or rape the woman. Or because the woman might feel like her privacy has been violated. Or the woman might feel nervous around the stalker, not knowing what they want.

None of these bad situations were going to result from this type of information-gathering. The engineer was not planning to hurt this woman or interfere with her in any way. The woman would not feel that her privacy has been violated, because they just want her name, and the woman probably wouldn’t mind if the bet-taker just told the engineer her name. And the woman knows what this “stalker” wants – to win a one-time bet. So she won’t be nervous about his intentions – winning a bet to find out a name is a harmless action that does not inspire worry.

As for posting her information online, yes, it seems like the engineer had an unintentional privacy leak in that they showed Facebook users from her high school her picture. (I don’t think he was purposefully lying about posting her info, I think he just didn’t consider the photo significant.) Showing the photo could be bad if the woman didn’t want anyone seeing that dress she bought, or didn’t want her alumni to be reminded of her. You could argue that showing the photo to those users was a mistake on the engineer’s part.

But you should keep in mind that the chances were pretty low that this woman’s picture leaked anything significant to her former high school classmates. It’s very likely that they didn’t care what dress she is wearing. Many of them saw her face already when she was actually in high school, and as for the ones who had not, seeing a normal photo of a random woman in a dress is unlikely to cause anything bad. There was a possibility, but it was very low.

You say no privacy violations "were going to result from this type of information-gathering". However you then concede that it resulted in a "privacy leak in that they showed Facebook users from her high school her picture," mentioning several reasons why the target may find this invasive. You frame it as "unintentional", but that is irrelevant; you've contradicted your claim.

I would certainly not argue that the critereon is intent to do physical harm, which is how you define "stalking". Boy, would an awful lot of stalking no longer be considered "stalking" under that definition. By your definition cyberstalking is ok if you only want to date them and/or joke with your bros about it, not rape someone.

Rather the issue is whether the actions of, say, posting your photo in a Facebook ad campaign -- and otherwise pursuing means of "information-gathering" so extraordinary that one needs to post to Hacker News to explain them -- might reasonably considered a willful invasion of a person's privacy. Certainly it could be, and these guys just didn't care, because they're just having a laugh, and she's probably cool with it, and if she's not, well screw her because girls should be cool with that sort of thing.

"stalk [verb]: to follow, watch, and bother (someone) constantly in a way that is frightening, dangerous, etc."

-- merriam-webster

This very much was not the case.

If it makes you feel better, the ad was also taken down very quickly.

This would be much more meaningful if you hadn't already stated that you took it down because you already got the information you wanted.

Yeah, no one would ever possibly be creeped out by that.

You think it's ok because you have good intentions. Guess what? So does every other creep. It's not up to you to decide whether your actions are frightening. You took a bet that you could stalk (message all her classmates!) and dox (post her picture online!) a girl without her permission and without even the slightest self-awareness that it's invasive behavior. And then you tried to lie about key details.

You, sir, are exactly the kind of male-privileged "brogrammer" that is giving this industry a bad name these days.

Also the ad didn't say that she was flirting with anybody and it was designed with an attempt to not make her look bad in any way.

Finally, she is aware of the whole deal and has been a good sport, and is not upset.

You said you didn't post any of her info online.. you ran a friggin Facebook ad campaign with her picture on it (which you obtained not from her)! Now you've just edited your comment to say you didn't post any other info about her that you obtained.

You did all this without her permission, according to your colleague. Now you're trying to weasel out of that too with ambiguous phrases like "she is aware". Yeah, after you told her what you already did.

Did it not even occur to you that it could be potentially embarrassing or invasive? What if she wasn't cool with it? What if she's just playing cool because you forced her hand? It's wrong of you to assume it's ok to cyberstalk someone for "fun" because your intentions are good -- your intentions being having a laugh with your bros.

The other point here, even if you think bro'ing out like this is perfectly acceptable workplace behavior / way to treat women, is that it's just incredibly stupid for a startup to tarnish their brand this way. Just don't do it.