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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
Ya waylata laytanee lam attakhith fulanan khaleelan
Transliteration-2
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.
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