Dating someone inexperienced
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Initially they manage to come off as calm and charming and make a good impression, but then fall apart when the stakes get higher.The reason this happens is that when they first run into that women she's new and they haven't had time to overthink things and attach any nervous feelings to her yet.
But when a guy is really shy his nervousness is at a level where it usually prevents him from doing any of those things.
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.
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.).
Unsurprisingly, they're really nervous and hesitant about this as well. They may have a blatant, all-systems-go opportunity where the girl is clearly interested, but they can't manage to go through with it.
There they are, sitting on a couch watching a movie with their date when the credits start to roll.
The scenario then goes in one of the following directions: They're too nervous to talk to her again; They do talk to her, but they're such a withdrawn, obvious wreck that she's not interested; They talk to her, but are too nervous to be themselves, end up acting like a goofball, and shoot themselves in the foot; They're so nervous that at that immediate moment escaping the anxious symptoms takes precedence over anything else, and they act rude or aloof towards her to purposely sabotage their chance.
This 'setting them up, but not following through' scenario can happen to different degrees.
Sometimes a guy will be able to talk to someone he's interested in, often because the circumstances put them together, so the onus wasn't on him to approach anyone.