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I think you should always respect personal boundaries, but it's precisely with those whom you are closest that you feel comfortable tinkering with those boundaries. If you never pushed the boundaries, you wouldn't have gotten so close to begin with. But once you find them, you never intentionally cross them too much - that would be a breach of trust.

[Edit] I write a little about the topic of play here: https://goo.gl/jHuUQn

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Exactly. The boundaries aren't disrespected - they change as relationships change. Disrespect for boundaries is a disrespect of the person whose boundary you are crossing. If you do it out of ignorance then it can often be forgiven and trust can be rebuilt if you show you can be trusted, but if it is repeated, knowing, or as a display of power, the relationships get worse - not better.

You are okay with a close friend touching you on the shoulder or asking personal questions because your relationship has evolved to a point where your boundaries permit it. It is not okay for a person you dislike to do those things because your relationship is such that your boundaries forbid it.

> you never intentionally cross them too much

I think the 'too much' is key - occasionally, you should cross them a little. But the opposite happened in the story - he was expanding his kid's boundaries.

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