Praise be to Allah.
Firstly:
One of the obligatory acts of ‘umrah is to enter ihram from the miqaat. If someone is in Makkah and wants to do ‘umrah, his miqaat is the area beyond the boundary of the Haram zone. So he should go out to any part of the area beyond the boundary, such as at-Tan‘eem or elsewhere, and enter ihram from there.
If someone who is inside Makkah enters ihram, he has failed to do one of the obligatory acts [of ‘umrah], and must offer a compensatory sacrifice. If he is unable to do that, he must fast for ten days, by analogy with the one who does Hajj tamattu‘ [i.e., entering ihram for ‘umrah, exiting ihram after ‘umrah, then entering ihram again for Hajj].
It says in Sharh Muntaha al-Iraadaat (1/525): And the one who is in Makkah should enter ihram for his ‘umrah from the area beyond the Haram boundary, because the Prophet (blessings and peace of Allah be upon him) instructed ‘Abd ar-Rahmaan ibn Abi Bakr to take ‘Aa’ishah to resume her ‘umrah from at-Tan‘eem. Agreed upon.
Moreover, all the actions of ‘umrah take place inside the Haram zone, so there is no alternative but to enter ihram from beyond the Haram boundary, so that he can combine both. This is in contrast to Hajj, when the pilgrim goes out to ‘Arafah, so he combines both.
But his entering ihram for ‘umrah from Makkah is valid, although he – meaning the one who enters ihram for ‘umrah from Makkah – must offer a compensatory sacrifice, because he failed to do an obligatory action, like the one who passes the miqaat without entering ihram. End quote.
Based on that, you must offer a compensatory sacrifice, to be slaughtered in Makkah and the meat distributed to the poor of the city.
Secondly:
The muhrim [pilgrim in ihram] must refrain from wearing tailored garments. The one who did ‘umrah in his ordinary clothes has committed an infraction, and he must repent and offer a fidyah. For this fidyah he has a choice: he may sacrifice a sheep, or feed six poor persons, or fast for three days.
Thirdly:
Shaving the head or cutting the hair is part of the rituals [of ‘umrah], and the muhrim cannot exit his ihram for ‘umrah except by doing it.
It says in al-Insaaf (4/56): Then he should do tawaaf (circumambulate the Ka‘bah) and sa‘i (go back and forth between as-Safa and al-Marwah), then shave his head or cut his hair, then he has exited ihram. Does exiting ihram come before he shaves his head or cuts his hair? There are two views, the basis for which are the two reports about Hajj: Is shaving the head or cutting the hair one of the rituals, or is it just to permit the pilgrim to do that which was not allowed during ihram, as mentioned above. This was mentioned by the commentator and by Ibn Maajah.
We noted above that the correct view is that it is one of the rituals, and the correct view here is also that it is one of the rituals, so the pilgrim cannot exit ihram except by doing one of the two. This is our view, which he classed as sound in at-Tasheeh and elsewhere, and stated definitively in al-Wajeez and elsewhere.
The second report is that it is just to permit the pilgrim to do that which was not allowed during ihram, so he should exit ihram before doing it, as mentioned in al-Hidaayah, al-Madhhab and at-Talkhees. End quote.
Based on that, if someone did not shave his head or cut his hair when he did ‘umrah, he is still in ihram; he must take off his tailored garments, shave his head or cut his hair, but he does not have to do anything with regard to any infractions that he may have committed, if he was unaware of the ruling.
Fourthly:
The one who did not shave his head or cut his hair is still in ihram, as we noted above. If he did a subsequent ‘umrah in which he shaved his head or cut his hair, then he has exited from the ihram of the first ‘umrah by virtue of that shaving his head or cutting his hair, and the second ‘umrah is null and void, because he entered ihram for it when he was still in ihram for the first ‘umrah.
Al-‘Izz ibn ‘Abd as-Salaam said in Qawaa‘id al-Ahkaam (p. 252): If someone entered ihram for two Hajjs or two ‘umrahs, or he wanted to incorporate one Hajj with another, or one ‘umrah with another, or he intended to pray two Zuhr prayers at the same time, it counts for him as one Hajj or one ‘umrah, but his prayer does not count. End quote.
We asked Shaykh ‘Abd ar-Rahmaan al-Barraak (may Allah preserve him) about a woman who did ‘umrah, but she forgot to cut her hair, then she went and entered ihram for another ‘umrah and did tawaaf and sa‘i, then she cut her hair.
He replied: Incorporating one ‘umrah into another is not acceptable according to the fuqaha’ of the Muslims, so the second ‘umrah is null and void, and her cutting her hair will be counted as part of her first ‘umrah.
See the answers to questions no. 128712 and 95860.
Fifthly:
If someone enters into a marriage contract before shaving his head or cutting his hair following his first ‘umrah, and did not do ‘umrah again after that, then he got married when he was in a state of ihram, so his marriage contract is not valid.
An-Nawawi (may Allah have mercy on him) said in Sharh Muslim (9/193): The Prophet (blessings and peace of Allah be upon him) said: “The muhrim (pilgrim in ihram) should not get married, have a marriage arranged for him or propose marriage”.
Muslim mentioned the difference of opinion as to whether the Prophet (blessings and peace of Allah be upon him) married Maymoonah when he was in ihram or when he had exited ihram.
Because of that, the scholars differed concerning the marriage of one who is in ihram. Maalik, ash-Shaafa‘i, Ahmad and the majority of the scholars among the Sahaabah and those who came after them were of the view that the marriage of one who is in ihram is not valid, based on the hadiths that speak of this matter.
Abu Haneefah and the Kufans said: His marriage is valid, because of the hadith which tells the story of Maymoonah.
The majority of scholars gave different responses to the hadith of Maymoonah, the soundest of which is that the Prophet (blessings and peace of Allah be upon him) married her when he had exited ihram. This is what was narrated by most of the Sahaabah. Al-Qaadi and others said: No one narrated that he married her when he was in ihram except Ibn ‘Abbaas only.
Maymoonah, Abu Raafi‘ and others narrated that he married her when he had exited ihram, and they had more knowledge of the matter, because they were involved in the matter, unlike Ibn ‘Abbaas, and because they were more accurate than Ibn ‘Abbaas, and more numerous.
The second response is to interpret the hadith of Ibn ‘Abbaas as meaning that he married her within the Haram boundary, which is permissible. One who is within the boundary of the Haram may be referred to as “muhrim” even if he is not in a state of ihram per se. This is a phrase that is very common and well known. End quote.
So if your third relative got married before he did another ‘umrah in which he shaved his head or cut his hair, then he must repeat the marriage contract, which is a simple matter. So the wife’s guardian should do another marriage contract with him in the presence of two Muslim witnesses, and say: I give So and so to you in marriage, and your relative should say: I accept marriage to So and so.
Each of you must offer a compensatory sacrifice for not entering ihram from outside the Haram boundary, and a fidyah of your choice, for doing ‘umrah wearing ordinary clothes.
And Allah knows best.
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