Caution: Translations of Quran and Ḥadīth may lead to possible misapplications and misinterpretations. This site is intended for students of sacred knowledge that are proficient in comprehending classical Arabic and have a strong foundation in Islamic sciences. Also note that religious injunctions rely on several aspects beyond what one may glean through reading individual aḥādīth.
Qurʾān Bukhārī Muslim Nasāʾī Abū Dāwūd Tirmidhī Ibn Mājah Mālik Aḥmad Dārimī Ḥākim Ibn Ḥibbān Ṭabarānī Nasāʾī's Kubrá Bayhaqī al-Luʾluʾ wa-al-Marjān Ibn Rajab's Fifty Riyāḍ al-Ṣāliḥīn Aḥmad's Zuhd Suyūṭī
suyuti:2-539b – ʿMr
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السيوطي:٢-٥٣٩b –

"عَنْ عمرَ قال: جَالِسُوا التَّوَّابِينَ، فَإِنَّهُمْ أَرَقُّ شَيْئٍ أَفْئِدَةً".  

ابن المبارك، [ش] ابن أبى شيبة [حم] أحمد فيه، وهناد، [ك] الحاكم في المستدرك [حل] أبى نعيم في الحلية

See similar narrations below:

Collected by Aḥmad's Zuhd
ahmad-zuhd:631 – ʿAbdullāh > Bī > Wakīʿ > Misʿar > ʿAwn b. ʿAbdullāh

[Machine] Umar, may Allah have mercy on him, said: "Sit with those who frequently repent, for they are the gentlest of hearts."  

الزهد لأحمد:٦٣١ – حَدَّثَنَا عَبْدُ اللَّهِ حَدَّثَنِي أبِي حَدَّثَنَا وَكِيعٌ حَدَّثَنَا مِسْعَرٌ عَنْ عَوْنِ بْنِ عَبْدِ اللَّهِ قَالَ

قَالَ عُمَرُ رَحِمَهُ اللَّهُ «جَالِسُوا التَّوَّابِينَ فَإِنَّهُمْ أَرَقُّ شَيْءٍ أَفْئِدَةً»