The Practice of Giving: How to Practice Giving "Thusly"? In the Diamond Sutra (or Vajra Prajna Paramita Sutra) Buddha says to Subhuti:


  a Bodhisattva should not dwell anywhere when he gives. He should not dwell in forms when he gives, nor should he dwell in sounds, smells,
  tastes, tangible objects, or dharmas when he gives. Subhuti, a
  Bodhisattva should give thus: he should not dwell in marks.


Below the passage Venerable Master Hsuan Hua (pp.91-94 in the link) explains that this comes down to giving without being aware of or paying attention to:


the one who gives,
the one who receives, and
that which is given


I have read this explanation many times, have attempted to meditate on the matter, and have tried to practice such "giving thusly" actively by being kind, helpful, donating to charities when prompted and to beggars when asked on the street.

However, I cannot help but feel that the manner in which I give is ultimately still contrived and pre-meditated - not free of "conditioned deliberation".

Specifically silly thoughts such as: 


"Do I have any change on me to give to this person in the street? - I'll make sure to have change on me at all times in the future."


seem very contrived and not in line with the idea that one must simply "give". Mindfully, perhaps, but not based on logic, not purposefully, or, for that matter, ostentatiously.

Question

Does anyone have any advice in how to practice giving thusly? (practice in the sense of "get better at") 

References to relevant literature would be most helpful. We practice Tibetan Buddhism in our family, but as can be seen from the text above, I try not to be a stickler for school-purity.
Does anyone have any advice in how to practice giving thusly?


I think one needs to closely analyze the meaning of "thusly". It's valid to think of it as practicing charity with a serene, equanimous, AND wise mind. It doesn't mean one just carelessly gives to everyone, even if that means giving to evil people so that they'll have the means to carry on with their evil way. Remember the merits of giving is proportional to not only the mind state of the giver, but also that of the receiver:


  [The Buddha:] "I tell you, Vaccha, even if a person throws the rinsings of a bowl or a cup into a village pool or pond, thinking, 'May whatever animals live here feed on this,' that would be a source of merit, to say nothing of what is given to human beings. But I do say that what is given to a virtuous person is of great fruit, and not so much what is given to an unvirtuous person. And the virtuous person has abandoned five factors and is endowed with five". ~~ AN 3.57 ~~