Learn Hardcore Japanese: watasi ha kanasii tomodati wo warawaseyou to suru.

Using が would instead highlight 私 as the grammatical subject, often with a sense of contrast, new information, or focus (e.g. “I am the one who tries…”).

In a neutral, descriptive sentence like this, 私は “I (topic) …” is very natural. Also, in everyday conversation, 私 is often dropped entirely and you’d just say:

悲しい友達を笑わせようとする。
“(I) try to make my sad friend laugh.”

Does 悲しい友達 mean “sad friend” or “sad about my friend”? How does the adjective work here?

In Japanese, an adjective directly in front of a noun modifies that noun.

悲しい友達 = “a friend who is sad” / “my sad friend”
(the friend is sad)

It does not mean “I am sad about my friend.” For that, you’d need a different structure, e.g.:

友達のことで悲しい。
“I’m sad about my friend.”

Also, you could say:

悲しんでいる友達
which literally means “a friend who is (currently) being sad / is in the middle of feeling sad,” emphasizing the ongoing state.
悲しい友達 is a bit more straightforward and can sound slightly more “descriptive” or general, but in context it’s perfectly natural as “my friend who is (feeling) sad.”

Why is を used after 友達? Isn’t を the object marker for a verb like “to eat” or “to drink”? How does it fit with 笑わせようとする?

Yes, を generally marks the direct object of a verb. Here, the verb that takes 友達 as its object is the causative verb 笑わせる (“to make [someone] laugh”).

The underlying structure is:

友達を笑わせる = “to make (my) friend laugh”

Then we turn 笑わせる into the volitional form 笑わせよう and attach とする:

友達を (my friend as the object)
笑わせよう (try/make [them] laugh – volitional)
とする (attempt / try to do)

So 友達を is the object of 笑わせよう, which itself is inside the larger pattern 笑わせようとする.

Grammatically:
[私は] [悲しい友達を] [笑わせようとする]
Topic – object – verb phrase.

What exactly does 笑わせようとする mean? Can you break down the grammar?

笑わせようとする is made from several parts:

笑う – “to laugh”
Causative form: 笑わせる – “to make (someone) laugh”
Volitional form: 笑わせる → 笑わせよう – “will make (someone) laugh / let’s make (someone) laugh”
Pattern: V-volitional + とする – “to try to do V / to attempt to V”

So:

笑わせようとする = “to try to make (someone) laugh”

This pattern 〜ようとする is a standard way to say “try to do ~”:

勉強しようとする – try to study
逃げようとする – try to run away
起きようとする – try to get up

In your sentence:

悲しい友達を笑わせようとする
= “(I) try to make my sad friend laugh.”

Why do we need the volitional form 笑わせよう? Why not just say 笑わせるとする?

The pattern “try to do X” in Japanese is specifically:

V-volitional + とする

So you need the volitional form:

笑わせる → 笑わせよう
笑わせようとする = “try to make (someone) laugh”

笑わせるとする is not the usual way to express “try to make (someone) laugh” and sounds ungrammatical or at least unnatural in this meaning.

Think of ようとする almost as a fixed pattern:

しようとする – try to do
食べようとする – try to eat
言おうとする – try to say

What’s the difference between 笑わせる and 笑わせようとする?

笑わせる = “to make (someone) laugh”
– Focus on the action itself; it usually implies the action happens/succeeds.
- 私は友達を笑わせる。
  “I make my friend laugh.” (I do so, as a fact/habit.)
笑わせようとする = “to try to make (someone) laugh”
– Focus on the attempt, not necessarily on whether it succeeds.
- 私は悲しい友達を笑わせようとする。
  “I try to make my sad friend laugh.” (Maybe it works, maybe it doesn’t; the emphasis is on the effort.)

So 〜ようとする adds the nuance of attempt / effort.

Is the sentence talking about something I do regularly, or something I’m doing right now? How does tense work in 笑わせようとする?

The plain 〜とする in the non-past (dictionary form) can be:

habitual/general: something you usually/regularly do
narrative present: describing something happening in the present (often in written style or storytelling)

私は悲しい友達を笑わせようとする。 could be understood as:

“I (tend to) try to make my sad friend laugh.” (habit/characteristic)
or, in narrative context,
“I try to make my sad friend laugh.” (describing the current situation)

If you want to clearly show an ongoing current action, it’s very natural to use 〜ている:

私は悲しい友達を笑わせようとしています。
“I am trying to make my sad friend laugh (right now / these days).”

How would I say this more politely?

Change the main verb する into its polite 〜ます form:

Plain: 私は悲しい友達を笑わせようとする。
Polite: 私は悲しい友達を笑わせようとします。

If you want to emphasize the ongoing action:

私は悲しい友達を笑わせようとしています。

In normal conversation, you’d probably drop 私 if it’s clear from context:

悲しい友達を笑わせようとしています。
“(I) am trying to make my sad friend laugh.”

Can the word order change? For example, is 私は友達を悲しい笑わせようとする okay?

Japanese word order is more flexible than English, but you must not break up the adjective–noun unit incorrectly.

悲しい友達 is a single unit: “sad friend”
You cannot say 友達を悲しい笑わせようとする – that would be ungrammatical.

Acceptable variations keep units intact:

私は悲しい友達を笑わせようとする。
悲しい友達を私は笑わせようとする。 (slight emphasis on 私)
悲しい友達を笑わせようとするのは私だ。 (“The one who tries to make my sad friend laugh is me.” – more contrastive)

But wherever you put it, 悲しい must directly modify 友達.

Is it natural to say 私 here, or would a native speaker usually omit it?

In many everyday contexts, a native speaker would omit 私 if the subject is clear:

悲しい友達を笑わせようとする。

Japanese often drops pronouns when they can be inferred from context.

私は is perfectly correct; it just makes the subject explicit. In a textbook example or clear statement about yourself, including 私は is very common and helpful for learners. In real conversation, both versions are possible; omission is just more typical if “I” is obvious.

Are there other natural ways to say “I try to cheer up my sad friend” besides using 笑わせようとする?

Yes, you can express “cheer up” in a few ways, depending on nuance:

Using 元気づける (“to cheer up / encourage”):
- 私は悲しい友達を元気づけようとする。
  “I try to cheer up my sad friend.”
Using 励ます (“to encourage”):
- 私は悲しい友達を励まそうとする。
  “I try to encourage my sad friend.”
Keeping 笑わせる but paraphrasing in English:
- 悲しい友達を笑わせようとする。
  literally: “I try to make my sad friend laugh,” which is a common way to “cheer someone up.”

All of these are natural. 笑わせようとする emphasizes making them laugh; 元気づけようとする and 励まそうとする emphasize cheering up / encouraging more broadly.