Hi Rabbi What is the correct way to ask HaShem for something, do we keep asking until its granted ? - I feel like I am nagging and how do we know when whatever we requested has been answered? Like if I asked to come to Israel for Pesach, HaShem may not grant that, His answer maybe no, how do I know what He wants for me? Thank you

The Talmud (Berechot 54b-55a) says that it is a positive thing if a person prays at length. However, this is true as long as the person does not sit in expectation that his requests will be fulfilled.(See also Tosafot to Berachot 32b)The Talmud there also says that to expect Hashem to fufill your wishes "reminds" Hashem of one's sins because, as Rashi explains since this persons thinks he is deserving to be answered Hashem examines his merits. We can infer from here that we must have trust in Hashem that he hears our prayers, but it is wrong to put Hashem on a timetable as it were, waiting when He will fulfill our requests. We can make our requests but we shouldn’t think that He owes us. There is a famous story of Choni Hame'agel, (the circle drawer see Ta'anit 19a) where Choni puts forth an ultimatum to Hashem that he will not leave the circle he drew until Hashem answers his prayers and grants the Jewish people rain. When it finally rained , he had additional requests and did not stop until he was completely satisfied. The Talmud says though, that if it were not for his extreme piety and being so close to Hashem that he is able to ask something like a child from a parent and have his request granted he would be excommunicated. We know what Hashem wants from us by learning the Torah and Halacha and thereby knowing what we are required to do. When we have many issues at hand our not sure what has priority we should consult a Rabbi, preferably one we know personally in order to get the best guidance.