صلاة الاستخارة is a prayer ordained for when we go through a situation we go through and are undecided, or if we've already decided a matter.
It is 2 Rak'ah other than the obligatory prayers. Avoid praying them at the forbidden times (When the sun is rising, setting, or at the meridian). But if it is impossible to wait, and you have to take the decision immediately, then pray it.
هم has two meanings:
1) Concerned
2) Intending to take an action.
This is why the scholars differed.
The Prophet taught the istikharah like he taught the Qur'an.
Say the Dua in Arabic, but when mentioning the matter, if you don't know how to say it in Arabic, you can say it in your tongue.
Then go ahead and take the action, but there are mistakes which people do:
1) Many people believe that this prayer should be followed by a dream. The Prophet never said it, but if it happens they you see something then it's okay, but it's not a condition. But if they don't dream and they wait and wait, delaying taking the action, because they didn't see a dream.
2) Asking others to pray on your behalf.
There are daughters who are getting married and the mother does the اسجتخارة. This isn't right. No one should offer it on behalf of anyone else, because the Prophet said, "Whoever is concerned let HIM...."
If you are concerned then pray for that person, but don't do the استخاره on her behalf.
3) People think it is only prescribed for great matters.
Jabir, who narrated the Hadith, said the Prophet would teach them to make it for all their affairs, both minor and major.
Even if you are confused whether you should buy a shoelace you can make it. We are humans, we don't know what is good for us, so consult Allah.
Even if you don't know whether advising someone will be good or not, then make صلاة الاستخاره.
In Taymiya said, "Whoever consults Allah will never regret it"
4. When some people make الاستخاره and something unpleasant happens they say, "I made الاستخاره and look at what happened"
Or some people will say, "I get no benefit or result"
They are thinking bad about Allah and not submitting to what Allah decrees for them after they consult him.
Ibn Umar said, "A man would consult Allah and Allah would choose for him, the man would be discontent, but later discover that what Allah chose for him is better"
"I don't care about what I love or hate, because what I hate may be good for me, and what I love may be bad for me" - Umar
Allah is الحكيم. Whatever He decrees for you is the best for you and what suits you. You consulted Him and He chose for you.
Just because it is contrary to what you like, it doesn't mean it's not the best choice for you.
One should not hate whatever Allah decrees for him after praying.
(2:216)
عسى ان تكرهو شي و هو خير لكم...
A man may pray istikharsh to get married to a woman he likes. And Allah may make it difficult for him. He doesn't know there is destruction in that matter for him.
Accept Allah's decree. It is a test. He may give you something better.
5. The scholars are in dispute with regards to where a person should say the dua. The majority say it is after تسليم. Ibn Taymiya was of the opinion that it should be said after the Tashahud and before تسليم because the Prophet used to invoke Allah during that position, and the person is still in the praying state.
Both are correct. You may say it before or after, but the people who say to do it in sujood is not a strong opinion.
"Let him offer two rak'ah ثم..."
Note: in case the person is unable to pray, it is enough for her to say the dua.
Note2: it is permissible to make an intention to pray الاستخاره at the same time one intends to pray a voluntary prayer.
If you are offering Duha for example, and you want to make istikharah you can join your intentions for one prayer.
It's better to be offered independently.
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