For a date to go well, you need to be present and focused. If you are over-tired, exhausted, or distracted, the dating can fall flat. If possible, it is best to begin dating when you are willing and able to apply the necessary time, energy, and clear mind to the project. It is not advisable to start the shidduch process if, for example, you are committed to being a head counsellor in three weeks, as there is too great a risk that things will be left hanging.
Making this most important decision of your life is not best done under pressure. If you are in the middle of a shidduch, and you find you are unable to reach a decision by a particular deadline, it is best to put things on hold and resume when you are again able to give dating your full attention.