komatta toki ha, enryosinaide watasi ni renrakusite kudasai.

困った is the past form of 困る (to be troubled / to be in difficulty), but before とき it does not simply mean past time in the same way English past tense does.

In Japanese, when a verb comes before とき (when), the form helps show the timing:

• 困るとき = when you are about to be troubled / when you get troubled
• 困ったとき = when you are troubled / when something has already become a problem

So 困ったとき feels natural for when you’re in trouble or when something comes up and you need help.

とき means time or when.

So:

• 困ったとき = when you’re in trouble
• 困ったときは = as for when you’re in trouble...

The は adds a topic/contrast feeling. It sets up the situation and then gives advice or instruction about that situation.

So the sentence structure is basically:

• As for when you’re in trouble, ... please contact me without hesitation.

Both are possible, but は gives a clearer topic-setting feel.

Compare:

• 困ったとき、連絡してください。
  = When you’re in trouble, please contact me.

• 困ったときは、連絡してください。
  = As for when you’re in trouble, please contact me.
  This can sound slightly more like advice, guidance, or a standing instruction.

The は can also add a mild contrast, as if implying:

• At least in that case, please contact me
• If that happens, then contact me

遠慮する often means to hold back, to be reserved, or to hesitate out of politeness.

So 遠慮しないで means:

• don’t hesitate
• don’t hold back
• don’t be shy about it

This is a very common expression when encouraging someone to ask for help, take something, or speak freely.

In this sentence, it means the speaker is reassuring the listener:

• Please don’t feel like you’re bothering me.
• Please contact me freely if you need to.

Good question. Both are possible, but the structure here is a little different.

This sentence uses:

• 遠慮しないで
  • 私に連絡してください

That means:

• Don’t hesitate, and please contact me.

The ～ないで form often means without doing X or don’t do X, and instead do Y.

So the flow is:

• without hesitating → contact me

If you said 遠慮しないでください, that would directly mean please don’t hesitate, and then you could add another sentence. But in this sentence, 遠慮しないで smoothly connects to the main request 連絡してください.

Because 連絡する takes the person contacted as the target/recipient, marked by に.

• 私に連絡する = contact me
• 先生に連絡する = contact the teacher

So に marks the person you direct the contact toward.

Using を here would be incorrect in standard Japanese.

連絡する is a suru-verb meaning to contact or to get in touch.

Its て-form is:

• 連絡して

Then ください after the て-form makes a polite request:

• 連絡してください = please contact me

This is one of the most common polite request patterns in Japanese:

• 待ってください = please wait
• 見てください = please look
• 教えてください = please tell me

So:

• 連絡して = contacting / contact and...
• 連絡してください = please contact

It could be omitted if the context is clear.

Japanese often leaves out things that are understood. So a shorter version could be:

• 困ったときは、遠慮しないで連絡してください。

That would still usually be understood as contact me, especially if the speaker is the obvious person.

However, including 私に makes it explicit and reassuring:

• Please contact me
• not just please make contact with someone

So in this sentence, 私に adds warmth and clarity.

The subject is omitted, which is very normal in Japanese.

The listener is understood from context. In English, you would naturally say:

• When you’re in trouble, please contact me without hesitation.

But in Japanese, you often does not need to be said. The sentence directly addresses the listener through the request form ください.

So even without あなた, the meaning is clear.

It is polite but warm.

Here’s why:

• 連絡してください is a polite request
• 遠慮しないで sounds friendly and encouraging
• 私に makes it personal and supportive

So this sentence would fit situations like:

• a teacher speaking to a student
• a coworker speaking politely to another coworker
• a senior helping a junior
• someone offering support in a kind but not overly stiff way

It is not casual, but it is also not extremely formal.

Yes, but the nuance is slightly different.

• 困ったとき = when you’re in trouble / when something has gone wrong
• 困っているとき = when you are in the state of being troubled

困っているとき focuses more on the ongoing condition.
困ったとき is very common and natural for general advice like this.

In many real situations, both could work, but 困ったときは sounds especially natural as a set phrase meaning if you run into trouble.

Not really in the sense of two fully separate commands. It is more like:

• Don’t hesitate, and contact me
• Contact me without hesitation

The first part modifies the feeling or manner of the second part.

So rather than thinking of it as:

1. Don’t hesitate.
2. Contact me.

it is often more natural to understand it as:

• Please contact me freely / without holding back.

No, normal Japanese is usually written without spaces between words:

• 困ったときは、遠慮しないで私に連絡してください。

The spaced version is probably just for learners, to help show the parts of the sentence.

Japanese normally uses a mix of kanji, hiragana, and punctuation to make word boundaries easier to read, so spaces are usually unnecessary.