Title

Intonation Notes:
1. すまない.
2. すみません.

Orthography Note: Writing the verb stem in Kanji as 済 is rare. 

1. 先日は会議に遅れてしまって本当にすみませんでした。
I'm really sorry for being late to the meeting the other day.

2. まじすまんかった！(Extremely Casual)

I'm really sorry about that!

3. すみません、通してください。
Excuse me, could you let me through?

4. 間違えてしまってすみません。
I’m sorry for messing up.

5. 混乱させてしまってすみません。
I’m sorry for confusing you.  

6. すみません、お時間よろしいですか。
Excuse me, but could I take a little bit of your time?

7. すいません、お勘定お願いします！
Excuse me! Check, please!

8. 大変すみませんでした。
I’m terribly sorry for what had happened.

Usage Notes:

1. The plain forms exist because people can still tell equals, people below them, or friends that they've been rude somehow. Additionally, there are grammatical circumstances, for instance, modifying a noun like とき (when), in which the verb cannot be in a polite conjugation. 

2. 失礼します is the go-to phrase for when hanging up on someone. 

Intonation Note: The intonation of shitsurei 失礼 is しつれい.

9a. 長文失礼しました。
9b. 長文すみません（でした）。
I apologize for (how I wrote) this long message.

Sentence Notes: 

1. 9a and 9b are very similar in nuance with 9a being more polite than 9b. The difference as to why でした is not necessarily obligatory with すみません but is with 失礼 lies in a very finite difference between the two words. 

2. Firstly, 失礼する literally means "to do something that is impolite." Remember that "non-past" covers what in English would be either "present tense" or the "future tense" When referring to an action in the moment, Japanese verbs will always translate as "I am going to do X." So, 長文失礼します, if you were to use it, would need to be at the start of the document you're sending. This is because the long text is coming up. 

3. Vice versa, when you've already written it and the person had to go through the struggle of reading it all, you mark your discourteous "past" behavior with 長文失礼しました.

4. As for すみません, you are recognizing that there could have been a better way of handling the situation. Perhaps you could have condensed your message down. At any rate, you're showing remorse for the situation not being ideal at the end of the day, but that lack of satisfaction isn't a thing of the past to you, the writer, necessarily. 

5. If you were to use すみませんでした, you're basically cutting off these logical loose ends by apologizing, albeit still politely, for doing something that wasn't the most ideal way of going about it. 

10. 失礼しました。申し訳ありません。
Please excuse (my behavior/action). I am terribly sorry*.

*: The literal definition of 申し訳ありません is to be explained next.  

11. 先日は失礼したね。
Sorry for how I was rude the other day.

12. 「Now, if you'll excuse me」とはお先に失礼する時の丁寧な表現です。

"Now, if you'll excuse me" is a polite phrase for when you are excusing yourself first.

13. メールにて失礼いたします。
Excuse me for the e-mail.

14. 大変失礼いたしました。今後は注意いたします。
I am terribly sorry for doing that. I will be careful moving forward.

Another phrase for "I'm sorry" is 申し訳ありません. This phrase literally means "I have no excuse," and it is considered more formal than a simple すみません and even used in conjunction with 失礼しました as we saw in Ex. 10. It, too, is altered in the same ways as the phrases before depending on speech level and the exact circumstance regarding your apology. 

Grammar Note: Because the plain form 申し訳ない utilizes adjective grammar, there are two ways to conjugate it in polite speech. Choosing to switch out ない for ありません will always be more polite than conjugating ない as a regular adjective then following it with です. Even so, both means are equally common.

Orthography Note: ございません（でした） is frequently spelled with the Ateji 御座いません（でした）, but for readability, it is not used in the examples below. 

15. お忙しいところ、大変申し訳ございません。
I deeply apologize for this while you’re busy.

16. 先日の忘年会では、酔いに任せて大変な（ご）無礼をして、申し訳ありませんでした。
At the year-end party the other day, I let alcohol get the best of me, in which I was very out-of-place, and I deeply apologize.

Grammar Note: 無礼 is an adjectival noun which means “impoliteness,” and is synonymous with 失礼, although it isn't used when excusing yourself when leaving.

Although the prefix ご often attaches itself to applicable nouns/adjectival nouns within a sentence to elevate the overall politeness level to honorific speech, when combined with negative words regarding one's own action, it is considered unnatural by some speakers. This is why you don't see ご失礼.  

17. 度重なる失礼、大変申し訳ございませんでした。
I am terribly sorry for how I’ve repeatedly been discourteous.

18. お客様には大変ご迷惑をおかけして申し訳ございません。
We are terribly sorry for the trouble we’ve placed you, our customer(s).

Sentence Note: Though the offense to customers would have been done in the past, the use of the non-past tense emphasizes the speaker’s current sense of guilt.

申し訳なく存じます

In incredibly humble language in which you are profusely apologizing for terrible lack of forethought, you may see 申し訳なく存じます (past tense → 申し訳なく存じました). The verb 存じる is the humble form of 思う (to think). So, literally, this phrase can be translated as "I believe (what I have done) is/was inexcusable." 

19. 運営に関して、行政側のミスが数件あり、消防団の皆様に申し訳なく存じました。今後はそうしたことがないよう、さらに注意を徹底してゆきたいと存じます。
There have been several cases of mishaps on our administrative side regarding operations, and I believe they have all been inexcusable to all of you in our fire department. Moving forward, I wish to be all the more thorough so that those sort of things don't happen again.

20. いつも何かとご無理をお願いし、申し訳なく存じます。
I am really sorry that I keep asking you to do the impossible (too much).

In very formal situations, you may hear the phrase お詫び（を）します. The verb 詫びる means "to apologize," and お詫び（を）します is its humble rendition. You will especially hear this used by people in power apologizing for their administration's mishandling. 

In addition to this humble form, you may replace します with either いたします or even 申し上げます to be further humble yourself, the latter being the most humble you can get, as you are declaring your apology. 

As has been hinted via the example sentences, there are other verbs meaning "to apologize," each possessing its unique nuance of apology. 

Grammar Note: The Kanji 謝 may either show gratitude or an apology depending on the word it's in, which is why it is utilized so much in this lesson.

Grammar Note: It is possible to hear/see the particle を in between the Sino-Japanese noun and the verb する in the expressions above. It often helps as a filler word as the person is trying to make their apology come out just right. 

31. 私が代わりに謝ります。
I shall apologize on (that person's) behalf.

32. みんなの旦那って謝りますか？
Does everyone's husband apologize?

33. 健太郎は外見んでは謝まっているが、｛謝る・お詫びの｝気持ちが一切感じられない。
Kentaro may be outwardly apologizing, but I feel absolutely no feeling of remorse. 

34. 先生が謝ってくれません。
My teacher won't apologize.   

35. お名前を書き間違えたことを陳謝｛します・いたします｝。 
I/we apologize for misspelling your name. 

36. 今回の件を厳粛に受け止め、陳謝いたします。 
We are solemnly coming to grips with this case and apologize (for what has happened).

37. これまでに誰かに謝罪（を）したことはありますか。
Is there anyone you have apologized to up to now?

Even in English, saying "my bad" as an apology is very casual, but the same thing is actually done in Japanese with the adjective 悪い. In very casual conversation, you may even hear it pronounced as わりぃ. 

39.  あ、わりぃ。
Oops, my bad.

When entering someone's home, room, office, or entryway, speakers will say 邪魔します to that person. The noun 邪魔 means hindrance, implying that one’s presence can be perceived as intruding on that person’s turf. 

It can be used in the past tense (～しました・いたしました) whenever one feels it’s necessary to leave after having clearly inconvenienced the other person. Or, it can also be seen in the progressive form (～して[います・おります]), especially by those in cleaning services when workers are busy tidying up your space despite you having arrived.

Grammar Note: Options in parentheses are ordered from least to most humble.

43. お邪魔じゃまします。
Excuse me for disturbing/interrupting you.

44.  お邪魔しております。
I apologize for being in the way.

45. お邪魔しました。
I’m sorry for having disturbed you.

It is also possible to hear 失礼します used in a similar fashion, but in this situation, you instantly become face to face with the listener and follow it with a request.

46. 失礼します、お手隙ですか。
Excuse me, are you free?

ごめんください

When entering someone's place without that person having not come to great you, it is customary to say ごめんください. An even more formal form of this is ごめんくださいませ, but this form is actually more commonly used as a means of hanging up in the customary service industry as a far more polite version of 失礼します.

47. ごめんください。田中さん、いらっしゃいますか。
May I come in? Are you there, Tanaka-san?

48. ごめんくださいませ。
I’m hanging up now./May I come in?

The standard phrase for saying “my condolences” is not お気の毒に, although it has gained some recognition as meaning such in the Western world. In reality, it is often interpreted as being too sarcastic or apathetic. The original meaning of 気の毒 is "poison to one's emotions," which became extended to showing sympathy to other people's misfortune. Alas, the world is cruel, and even in English "that's too bad" or "what a pity" are usually deemed sarcastic in the same way. 

49. それはお気の毒に・・・
What a pity/that's too bad...

お気の毒に思います and お気の毒に存じます are the polite and humble forms respectively, which are less likely to be taken sarcastically. 

50. 事故に遭われたと聞いて、お気の毒に【思います・存じます】。
I'm sorry to hear that you got in an accident. 

You can also see お気の毒な - as an adjectival noun - where it has more leverage. 

51. 被災された方にはお気の毒で言葉がありません。
I feel so bad for those victims of the disaster that I have no words.

You may also opt for お気の毒様｛です・でした｝. There is hardly any difference in nuance between using the non-past and past form other than the speaker being more detached from the situation when the past tense is used. 

52. 救急隊の人たちは今回お気の毒様でした。
My condolences really were with the first responders this time. 

53. 事故に遭われたとは、お気きの毒様でした。
I am terribly sorry to hear that you were in an accident. 

Even so, there are other phrases that won't cause hard feelings. For instance, you could say ご心中お察し申し上げます, which translates as "you have my sympathies." 

54. この度は誠にお気きの毒様です。
Please accept my sympathy at this time.

ご愁傷様

Another important phrase used toward people who have gone through a terrible loss or misfortune including the loss of a loved one is ご愁傷様｛[です/でした]・[でございます/でございました]｝. The use of the past tense is typically used most often when this is all the speaker can think of that's appropriate to say, whereas the use of the non-past tense is best used when the speaker feels compelled to speak more about the matter. 

55. この度は誠にご愁傷様でございます。

My truest and deepest sympathy goes out to you at this time.

Similarly to how phrases utilizing お気の毒 have become sarcastic in tone in recent times, so has ご愁傷様. Of course, tone is everything, but the most preferred phrase that you won't risk sounding sarcastic currently is: 

56. この度は心よりお悔み申し上げます。

My deepest sympathy from the heart at this time.

Curriculum Note: To learn more about how funerals are handled in Japanese culture, see this lesson.