In the case of Ben Schoen’s attempt at wooing of Grace Spelman, he assumed a far greater level of intimacy than actually existed; the only contact they had was that she friended him on Facebook when she was fourteen.
For nine years, they had contact; they never interacted on Facebook or Twitter until he tweeted at her out of the blue.
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Pushing and pushing for Spelman to respond to him, switching social media platforms when she wouldn’t respond to him on the previous one?
This is someone who’s demonstrating poor social calibration; he’s getting a very obvious brush-off and keeps trying anyway.
But learning to navigate the subtleties of these rules is part of developing your social calibration. As I’m always saying, being good with women is a skill and some people are going to be more skilled than others.
And speaking of which: Whenever we talk about times when it’s appropriate to approach or hit on women, people will inevitably bring up someone they know – either personally or friend-of-a-friend – who broke “the rules” successfully. The fact that Michael Jordan can pull off an astounding dunk doesn’t mean that should give it a shot.
The first message was relatively innocuous, but the ones that followed became weren’t – he was making the kind of jokes-but-not-really that assume a greater level of familiarity between the two than actually existed.
Two people who had at least a passing relationship online might get away with tweets like “For my birthday, I want @gracespelman to follow me back”; from a complete stranger, that’s just unsettlingly creepy.
It’s going to be an inexact process at best; it’s not as though grinding in bars gives you 120 XP per hour that culminates with your hitting the cap as a level 80 Pick-Up Artist.
As a general rule, the more successes you have – getting working phone numbers, first dates, second dates – the more risks you can reasonably take.
By that same token, there are times and places where the social context says that says that it’s acceptable to approach a stranger and that a person’s presence is a general acceptance of the social contract.