Ruling of praying Istikhaarah (i.e. seeking Divine Guidance) in several matters
14-1-2014 | IslamWeb
Question:
Is it permissible to pray Istikhaarah to choose between three matters?
Answer:
All perfect praise be to Allaah, The Lord of the worlds. I testify that there is none worthy of worship except Allaah, and that Muhammad, sallallaahu ‘alayhi wa sallam, is His slave and Messenger.
The Messenger of Allaah, sallallaahu ‘alayhi wa sallam, recommended performing Istikhaarah, taught it to his Companions and commanded doing it if one is deliberating about a decision.
Jaabir ibn ‘Abdullaah 
said: “The Messenger of Allaah, sallallaahu ‘alayhi wa sallam, used to teach his Companions to make Istikhaarah in all matters just as he used to teach them Soorahs from the Quran. He, sallallaahu ‘alayhi wa sallam, said: 'If anyone among you is deliberating about a decision he has to make, then let him pray two Rak’ahs of non-obligatory prayer, then say...'" [Al-Bukhari, An-Nisaa’i and Abu Daawood]
Accordingly, there is no harm in making Istikhaarah, seeking guidance from Allaah The Almighty regarding making a decision among three matters or even more. However, one should pray Istikhaarah only for matters he intends to see through and not just passing thoughts.
It was said in ‘Awn Al-Ma‘bood: “It may be that what is meant by deliberation here is resolve because a passing thought is not firmly established. Also, a person should not pray Istikhaarah except when he has decided to do something but does not have a strong inclination towards it. Otherwise, if a person were to pray Istikhaarah for every thought that crossed his mind, he would never stop and would waste all his time doing so.” [4/278]