Is it possible to combine a number of matters in one istikhaarah prayer?

Istikhaarah is a supplication (du‘aa’) in which the Muslim asks his Lord, may He be glorified and exalted, to choose for him the better of two things. According to Islamic teachings, the matter of supplication is broad in scope, and it is permissible for the Muslim to ask Allah, may He be exalted, in his supplication for all that he needs. The Prophet (blessings and peace of Allah be upon him) used to like concise supplications, which are those that include many meanings in a few words.

There does not seem to be any reason to disallow mentioning more than one matter in istikhaarah, after praying two rak‘ahs, and by doing so he will have done what is required of praying two rak‘ahs, then offering the du‘aa’ of istikhaarah regarding his need after that. However, it is better to have one prayer and supplication for each matter.

Shaykh ‘Abdullah ibn Jibreen (may Allah have mercy on him) was asked:

Can I pray istikhaarah for more than one matter in one prayer?

He replied:

That is permissible, and you can make the prayer a means to offer supplication after it, and there is no reason not to pray istikhaarah after praying [two rak‘ahs] with regard to two or more matters. So you may say in the supplication, after the introduction: “O Allah, if such and such a matter is good for me, and such and such a matter is good for me,” then say: “make them easy for me,” and so on.

Fataawa fi Salaat al-Istikhaarah (question no. 12).

We put this question to our shaykh, ‘Abd ar-Rahmaan al-Barraak (may Allah preserve him) and he said: He may combine a number of matters in one prayer, and say: O Allah, if You know that such and such, and such and such, and such and such are good for me…

And Allah knows best.