He notices she seems like she's becoming attracted to him, and he blows things soon after.
Hanging out, going on a date, the idea is the same.
They may never ask them out, or put it off so long that by the time they do they're well into the Friend Zone.
Even with all of the above stacked against them, a shyer, inexperienced guy will sometimes have enough things go their way that they end up in a position where they're alone with a woman and want to 'make a move' on them (e.g., kiss them, put their arm around them, etc.).
The first is when a guy simply sees a girl around a few times and makes confident eye contact with her.
She seems attracted and intrigued and like she's waiting for the guy to approach her.
They'll come away from the interaction feeling excited and optimistic about where things may lead.
Over the years several women have written me to tell me reading this site has helped them understand the actions of a shy guy they were pursuing.
I also wrote a follow up to this article on some of the unique issues shy women struggle with.
I'll break this down further below, but their central problem is that they're just really anxious, scared, and inhibited around women.
At other times it's more of a powerful, paralyzing hesitation.
Like they know how they want to act, but an invisible force field is preventing them from doing so.