How do you help someone shy getting into a relationship?

How do you help someone shy getting into a relationship?
This doesn't involve me directly.
There's a woman in my office that with time became part of my circle of friends, she's intelligent and good-looking but she's also very shy.
Her situation is that she likes a guy in our company and he seems to like her too, but despite the best efforts from all of us (especially me and the girl I'm going out with) to give her advice and some confidence, she still doesn't manage to get clear about it with him and as a results he's really confused by her mixed signals.
Today she went out with the girl I'm seeing and lamented she's not "capable of doing anything" and is frustrated because she never had a boyfriend and is still a "virgin at 25".

We honestly don't know what else to do to help her out, any suggestion?
How do you help someone shy getting into a relationship?
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