What is the proper way to write an Eszett on paper with a pen? In English we are told to start letters at the top, but the ß only has ends at the bottom, so what is the proper way to draw the letter?
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In German there is not a single "proper" way to write letters in handwriting. There are regional variations (see here for details).
For schools in Germany there are federal regulations that define how pupils learn to write. Most widely used are the "Lateinische Ausgangsschrift" and the "Vereinfachte Ausgangsschrift". In these the letter 'ß' is written as follows:
Somehow like that. It depends - as always - how the previous letter ended, and what the next letter is.
I just write it like my greek beta
There are some people writing it with an upstroke (quite similar to user unknowns proposal) like that: taken from WikiBooks German