Is it wrong to be a "people pleaser"?

What is wrong with pleasing others?

Nothing - unless we'd help them more by not pleasing them.

To what level should we care about others?

To whatever level we are able.

And what should we avoid?

Not caring about others to whatever level we're able.

Good householder, honored Buddhaparisada, interested,

Good and importand question, all along the path, till there, and it's end, unbound.

Yes, it is wrong if by unskilful means and for unskilful poor-pose. No, it isn't wrong, if by skilful means and for skilful pure-pose, good householder.

Most helpful and simple, everywhere and -when applyable, are the teachings toward the Sublime Buddhas son: Ambalatthika-rahulovada Sutta: Instructions to Rahula at Mango Stone.

Importand is maybe that one does only need to be pleasing for others, as long in relation, dependency of others: relation duties (next to skilful). To gain independency fulfilling the duties of ones relation are importand. Otherwise no end and lot of bad condition-accumulation.

To act most pleasing within ones sociaty is also called Sangha-vatthu (Ground of community): AN 4.32 Sangaha Sutta: The Bonds of Fellowship. (Btw one of the Suttas certain sects addopted fast for their worldly purpose, since powerful.)

There is a lot to talk about on this question, at least because the path is nothing but to gain highest "being" plrasing for all others and oneself, so here just an entrance for those wishing to be pleasing for higher and highest goal.

So called "people pleasure", addicted to try to make all perfect for others, are, for the most very caught and unfree, slaves of their desires and after certain rewards, seldom real giver. So good to think a lot about the issue, especially if accepting to harm oneself or others for "pleasing" here and there.

One is welcome to use possible more proper areas for more on it. At least because there are those pleasing things, unpleasing for others in their sphere of awareness: AN 5.157: Dukkathā Sutta: Unpleasant talk.

If serious free of certain amount of desires, this words by Ajahn Fuang may be of help (or hell for those not really free as well, so careful with it, it's wrong when gratitude, right view, is abounded at the same time, past, present, futur...):

"If people hate you, that's when you're let off the hook. You can come and go as you like without having to worry about whether or not they'll miss you or get upset at your going. And you don't have to bring any presents for them when you come back. You're free to do as you like (within skilful!)."

(Note: this isn't given to please anyone after trade, exchange, stacks and what binds in this wheel here, but for liberation from it)

One of the phrases I remember is from the Kalama sutta

Now, Kalamas, don't go by reports, by legends, by traditions, by scripture, by logical conjecture, by inference, by analogies, by agreement through pondering views, by probability, or by the thought, 'This contemplative is our teacher.' When you know for yourselves that, 'These qualities are skillful; these qualities are blameless; these qualities are praised by the wise; these qualities, when adopted & carried out, lead to welfare & to happiness' — then you should enter & remain in them.

So in terms of pleasing people, perhaps do what's praised by people who are wise -- and not necessarily what would "please" a person who is unwise.

There's a lot of specific advice -- which seems especially for laypeople, about good friends and bad friends -- in the Sigalovada Sutta.

I suppose you please people by saying things that are agreeable and endearing to them.

According to MN 58 below, it is not appropriate to say agreeable and endearing things, if they are unfactual and untrue.

From MN 58:

1. In the case of words that the Tathagata knows to be unfactual, untrue, unbeneficial (or: not connected with the goal), unendearing & disagreeable to others, he does not say them.

2. In the case of words that the Tathagata knows to be factual, true, unbeneficial, unendearing & disagreeable to others, he does not say them.

3. In the case of words that the Tathagata knows to be factual, true, beneficial, but unendearing & disagreeable to others, he has a sense of the proper time for saying them.

4. In the case of words that the Tathagata knows to be unfactual, untrue, unbeneficial, but endearing & agreeable to others, he does not say them.

5. In the case of words that the Tathagata knows to be factual, true, unbeneficial, but endearing & agreeable to others, he does not say them.

6. In the case of words that the Tathagata knows to be factual, true, beneficial, and endearing & agreeable to others, he has a sense of the proper time for saying them. Why is that? Because the Tathagata has sympathy for living beings."

This is an important topic.

AN4.95:1.1: “Mendicants, these four people are found in the world. What four?

There are those who practice to benefit neither themselves nor others. It creates no benefit. Let's skip that one.

And one can practice to benefit oneself. Or one can practice to benefit others. However...

AN4.95:3.3: But the person who practices to benefit both themselves and others is the foremost, best, chief, highest, and finest of the four.

Notice also that there is an important difference between pleasing others and practicing for their benefit. For example, a drug addict would be pleased to receive free drugs, but it would not be to their benefit. Let us all practice to benefit others as well as ourselves.