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Rambam writes in Teshuva 2,9 that one must ask a person for forgiveness when he has wronged him and personal Teshuva is not enough.

I have seen people (and I myself have often done this) asking for forgiveness in case they have done something wrong.

It is all a bit fake but everyone does it and I personally feel that this custom devalues the entire requesting forgiveness process.

I think it is obvious that one doesn't have to go around giving people money in case he once unwittingly damaged him. So what about when there is no money involved? I certainly hear a case of 'why not?' here, but perhaps it can cause embarrassment and reignite dormant feelings...

Is there a source to oblige asking for forgiveness when you don't know if you've done anything bad to this person?

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    I think this question delves into the general concept of Teshuva whether it is for sins done against G-d or man. Clearly, on Yom Kippur we ask G-d to forgive us for a whole list of sins that we are not sure if we have done. If we're asking G-d about a doubt, it seems to me that we should err on the side of caution and ask our friends to forgive us for doubts, as well. I can't see anything wrong with doing that. Also, keep in mind that Teshuva isn't just about for doing things wrong. It's about "missing the mark" and not doing things RIGHT towards your friend! There's nothing fake, here.
    – DanF
    Aug 24, 2017 at 17:07
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    Also, one can be perceived as having done wrong even though one may not realize it. For example, passing by someone without noticing him may be perceived as having ignored him. Thus, asking mechilah can fix what could have become a problem.
    – sabbahillel
    Aug 24, 2017 at 17:26
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    Many people recite a prayer before going to sleep that says that you forgive anyone who has hurt you whether intentionally or unintentionally, and all sorts of other "conditions". Here, you're doing the opposite. You've forgiven someone who hasn't even requested forgiveness! But, I would surmise that you may not recall every person who may have hurt you in some way during the day, anyway. So, there's doubt, here, as well.
    – DanF
    Aug 24, 2017 at 18:03
  • @Moshe I don't understand. You're never obliged to ask forgiveness. You just need to so he forgives you. So are you asking if you must ask forgiveness? No! Are you asking do I need to ask for forgiveness even if I dont know if I did anything wrong? Well it didn't matter if you know you did something wrong, to get full forgiveness he or she must forgive your as well. It's not the asking that forgives you it's his deciding to forgive you. Why would it matter if you know what you did or not?
    – Orion
    Aug 3, 2018 at 0:23

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It seems that a Leader or someone who is in a public position has to account for his actions and apologize publicly, and should someone come forward to proclaim monetary damage or using his position for his own benefit done to or hurt feelings/false accusing that he wrongly caused through misjudgment.

Bamidbar 16,15 says Moshe accounted for his actios saying he did not take any monetary benefit from anyone as Leader:
ויחר למשה מאד ויאמר אל יהוה אל תפן אל מנחתם לא חמור אחד מהם נשאתי

Likewise he did not mistakenly accuse anyone of wrong:
ולא הרעתי את אחד מהם
Bamidbar Rabbah explains 18,10: שלא חייבתי את הזכאי ולא זכיתי את החייב

Bamidbar Rabbah continues that Korach still blamed Moshe for taking advantage of his position
הלך קרח ואמר אני מבקש שתהא הגדולה על כלנו חוזרת שמשה נטל מלכות לעצמו והכהונה גדולה נתן לאחיו

And then it says further in Bamidbar 16,28 that Moshe said it was all from Hashem:
ויאמר משה בזאת תדעון כי ה שלחני לעשות את כל המעשים האלה כי לא מלבי

In Shmuel 1 12, Shmuel also makes a proclamation of innocence. הנני ענו בי נגד ה ונגד משיחו את שור מי לקחתי וחמור מי לקחתי ואת מי עשקתי את מי רצותי ומיד מי לקחתי כפר ואעלים עיני בו ואשיב לכם ד ויאמרו לא עשקתנו ולא רצותנו ולא לקחת מיד איש מאומה

A leader has to deal with everyone, if you know you have nothing to do with someone it seams OCD and over righteous to apologize in public or to people whom you know no history of misdemeanors between yourselves.

However ones wife/parents/brothers/sisters/close friends or any one with whom one sometimes lets down his guard and could act carelessly, then apologize in doubt.

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There certainly is a source for doing serious Teshuva on doubtful averios The Rema Orech Chaim 603 writes וספק עבירה צריך יותר תשובה מעבירה ודאי כי יותר מתחרט כשיודע שעשה משאינו יודע ולכן קרבן אשם תלוי הוצרך להיות יותר ביוקר מחטאת: (ד"ע ורבינו יונה ריש ברכות): * *And a doubtful aveira (sin) needs more repentance from a certain aveira, because one that knows regrets more than one who does not know (which is the case when one is unsure). And therefore the Conditional Asham Offering (Korban Asham Taluy - brought for certain sins possibly done via negligence) needs to be more valuable than a Guilt Offering (Korban Chatas - brought for sins knowingly done via negligence) [Rabbeinu Yonah, beginning of Brachos.]**

That certainly includes people who you may have inadvertently offended that you have to have to ask mechila from.

As far as giving money to people that you might owe to, it's alot easier to inadvertently hurt someone that to unknowingly owe them money. Even so, The Mishne Berurah (Shulchan Aruch, Orach Chaim 606, Seif Katan 1), discusses this concept and says that you should go to a Rav to figure it out before Yom Kippur and not rely on your own judgment. . וכ"ש אם יש בידו מן הגזל ואונאה וכל דבר הנוגע בממון יראה לתקן. [דזהו המקטרג הגדול על האדם כמו שאחז"ל סאה מלא עונות מי מקטרג גזל מקטרג בראש] ואם יש לחבירו בידו ממון שיש לו תביעה עליהם יודיענו אע"פ שחבירו לא ידע מזה כלל ועכ"פ יסדר לפני הרב ומ"ץ הענין בשלימות ובאמת בלא שקר ולשאול האיך להתנהג. כללו של דבר כל דבר שבממון לא יסמוך על הוראתו כי היצה"ר יש לו התירים הרבה [ח"

About money matters, you can go to a Rav. For inadvertent pain that was caused you can't so you should ask Mechila.

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  • I haven't had a chance to read your answer fully yet, but I think the question was more focused on a situation in which you didn't have a sofeik as such. You weren't thinking that you did X and that may or may not have caused insult. You didn't know you did anything in the first place. I suppose it might be more similar to doing teshuva for aveiros you don't know about. Even so, I'm not convinced that what we would apply to teshuva bein adam lmakom applies to requesting mechila. Your thoughts are appreciated.
    – Moshe Steinberg
    Dec 26, 2019 at 19:49

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