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Popular and/or Featured Works
Muhammad Asad   
Oh, woe is me! Would that I had not taken so-and-so for a friend
The Clear Quran, Dr. Mustafa Khattab   
Woe to me! I wish I had never taken so-and-so as a close friend.
Safi Kaskas   
Woe to me! I wish I had not taken so and so as a friend.

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Source Arabic and Literal tools
Arabic   
يَا وَيْلَتَىٰ لَيْتَنِي لَمْ أَتَّخِذْ فُلَانًا خَلِيلً
Transliteration (2021)   
yāwaylatā laytanī lam attakhidh fulānan khalīla
Word for Word
Dr. Shehnaz Shaikh, Ms. Kauser Katri, and more
  
O woe to me! I wish not I had taken that one (as) a friend.

Generally Accepted Translations of the Meaning
Muhammad Asad   
Oh, woe is me! Would that I had not taken so-and-so for a friend
M. M. Pickthall   
Alas for me! Ah, would that I had never taken such an one for friend
Yusuf Ali (Saudi Rev. 1985)   
"Ah! woe is me! Would that I had never taken such a one for a friend
The Clear Quran, Dr. Mustafa Khattab   
Woe to me! I wish I had never taken so-and-so as a close friend.
Safi Kaskas   
Woe to me! I wish I had not taken so and so as a friend.
Wahiduddin Khan   
Oh, would that I had never chosen such a one for my companio
Shakir   
O woe is me! would that I had not taken such a one for a friend
Dr. Laleh Bakhtiar   
Ah! Woe is me! Would that I take not to myself so-and-so as a friend!
T.B.Irving   
He will say: "It´s too bad for me! If I had only taken a pathway alongside the Messenger! It´s too bad for me! If I had not adopted So-and-So as a close friend!
Abdul Hye   
Oh! Woe to me! Would that I had never taken so-and-so as a friend!
The Study Quran   
Oh, woe unto me! Would that I had not taken so-and-so for a friend
Dr. Kamal Omar   
Ah! Woe to me! Would that I had not taken so and so as a friend
Farook Malik   
Oh! Would that I had never chosen so-and-so for my companion
Talal A. Itani (new translation)   
Oh, woe to me; I wish I never took so-and-so for a friend
Muhammad Mahmoud Ghali   
Oh, woe to me! Would that I had not taken so-and-so to myself for a (close) fellow
Muhammad Sarwar   
Woe to us! Would that we had not been friends with so and so
Muhammad Taqi Usmani   
Woe to me! Would that I had not taken so-and-so for my friend
Shabbir Ahmed   
"Oh, woe unto me, I wish I hadn't taken so-and-so for a friend!"
Dr. Munir Munshey   
"Alas! My misfortune! If only I had not taken that one _ (the Shaitan) _ as a friend!"
Syed Vickar Ahamed   
"Oh! I am (now in) misery! If only I had never taken such an (Evil) one as a friend
Umm Muhammad (Sahih International)   
Oh, woe to me! I wish I had not taken that one as a friend
[The Monotheist Group] (2011 Edition)   
"Woe unto me, I wish I did not take so and so as a friend!"
Abdel Haleem   
Woe is me! If only I had not taken so and so as a friend
Abdul Majid Daryabadi   
Ah! woe unto me! wouldthat had never taken such a one for a friend
Ahmed Ali   
Woe alas, ah would I had not taken so-and-so as friend
Aisha Bewley   
Alas for me! If only I had not taken so-and-so for a friend!
Ali Ünal   
"Oh, woe is me! Would that I had not taken so-and-so for a friend
Ali Quli Qara'i   
Woe to me! I wish I had not taken so and so as a friend
Hamid S. Aziz   
"O, woe is me! Would that I had not taken such a one for a friend
Ali Bakhtiari Nejad   
Woe to me, I wish I had not taken so and so as a friend
A.L. Bilal Muhammad et al (2018)   
“Oh, I wish I had never taken that one for a friend
Musharraf Hussain   
Woe to me! If only I hadn’t taken so-and-so as a friend;
Maududi   
O, woe to me! Would that I had not chosen so and so for a friend
[The Monotheist Group] (2013 Edition)   
"Woe to me, I wish I did not take so and so as a friend!"
Mohammad Shafi   
"Oh would that I had never chosen such-and-such as my friend!"

Controversial or status undetermined works
Ahmed Raza Khan (Barelvi)   
Ah' Woe to me', would that anyhow I had not taken such a one for a friend.
Rashad Khalifa   
"Alas, woe to me, I wish I did not take that person as a friend.
Hasan Al-Fatih Qaribullah   
Would that I had never chosen soandso for my companion
Maulana Muhammad Ali   
O woe is me! would that I had not taken such a one for a friend
Muhammad Ahmed - Samira   
Oh my calamity, I wish I did not take so and so (as) a faithful, close friend
Bijan Moeinian   
“Pity on me. If I had not taken so and so as a friend!”
Faridul Haque   
“Woe to me – alas, if only I had not taken that one for a friend.”
Sher Ali   
`O, woe is me ! would that I had never taken such a one for a friend
Dr. Mohammad Tahir-ul-Qadri   
Ah! Woe to me! Would that I had not taken such a one for a friend
Amatul Rahman Omar   
`Ah, woe is me! would that I had not made friends with so and so
Muhsin Khan & Muhammad al-Hilali   
"Ah! Woe to me! Would that I had never taken so-and-so as a friend

Non-Muslim and/or Orientalist works
Arthur John Arberry   
Alas, would that I had not taken So-and-so for a friend
George Sale   
Alas for me! O that I had not taken such a one for my friend
Edward Henry Palmer   
O, woe is me! would that I had not taken such a one for a friend now
John Medows Rodwell   
"Oh! woe is me! would that I had not taken such an one for my friend
N J Dawood (2014)   
Oh, would that I had never chosen so-and-so for my companion.

New, Partial, or In Progress Translations
Linda “iLHam” Barto   
“How miserable I am! I wish I had never made friends with old so-and-so.
Irving & Mohamed Hegab   
It's too bad for me! If I had not adopted So-and-So as a close friend!
Sayyid Qutb   
Oh, woe is me! Would that I had never taken so- and-so for a friend!
Ahmed Hulusi   
“Woe to me, I wish I had not befriended him (the body demon, the idea “I am the body” produced by the second brain in one’s gut)!”
Sayyed Abbas Sadr-Ameli   
Oh woe is me! Would that I had not taken such a one for a friend
Al-muntakhab fi tafsir al-Qur'an al-Karim   
And he adds: "Woe betide me, I wish I did not take such a man for a friend"
Mir Aneesuddin   
And on that day the unjust will bite his hands saying, "I wish I had taken a way with the messenger.

Obsolete and/or older editions
Yusuf Ali (Orig. 1938)   
"Ah! woe is me! Would that I had never taken such a one for a friend
OLD Literal Word for Word   
O woe to me! I wish not I had taken that one (as) a friend