Help me figure out how I lost this bet to an engineer

tl;dr -- fiverr

1. Compose tactful email text explaining the bet. This is optional if you don't care about tact or a potential negative impact on your or your company image.

2. Go to fiverr and get a person or three to find teachers, administrators, and students who were at the same high school around the same time. Have them send the letter you composed to these potential teachers, staff, and peers. Track with close.io.

3. Get answers and try to confirm results.

4. With new data, iterate text of email and/or task request for fiverr if appropriate.

If you are skilled at chatting up gatekeepers (many sales folks are good at this), then you can call the school admin, explain the situation to her, and the answer would be yours in a few minutes.

There are some other options that are of questionable legality and/or ethics, but I will stay away from those.

You guys absolutely have written about her flirtations in this blog post, which everyone who saw that Facebook ad can now link back to her.

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.

It's not impossible to "find out" about something before it's over, you know. The white knights in this thread need to calm down just a wee bit.

Perhaps she was doing a presentation, so was alone at the front of the room. The photographer, being in the audience, would obviously know which presentation it was and from there its a quick look-up on the list of presenters.

I think the engineer was not stalking her in any sense that matters. Looking up information on someone could be considered “stalking”, but if there was no likely bad outcome from it, then it’s harmless. In the same way, sneaking into a movie theater without a ticket is usually a bad thing, but if you actually bought a ticket and then you accidentally dropped your ticket in the gutter, your sneaking in is moral and acceptable. It’s all about the expected result, not the means you use.

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.