Spren of Kindness

Asking me anything involving any kind of social situation is like asking an Inkling how to swim. (I guess I'll rephrase that for people who haven't heard of Splatoon: asking me is like asking π how to act rationally.)

Depends on your personality, and the personality of the other person. My closest friends are people who hate large groups of people, but are super friendly in small, tight knit groups. If you want to get to know someone like that, then go ask them a question.

Examples?

Sports?

Favorite Disney Movie?

Musical Instruments?

Favorite Avenger?

Beaches or Mountains?

Once you have asked a question or two, then the conversation will begin to flow. 
I am friends with other people though, and I can interact with a lot of personalities (though I don’t always enjoy it). More outgoing people like jokes and humor. Makes jokes, insert yourself in comedically appropriate moments, and don’t second guess yourself. Be confident. For example, a good friend of mine was giving a “Shark Tank” presentation in Civics. It was an idea for an electromagnet powered generator. He said it would be eco friendly, so if you don’t use it you are evil (which was funny in its own). Someone asked if he said “evil” or “emo”. He clarified that he had indeed said emo, and then after a pause added “but there isn’t really a difference between the two anyway”. He would be terrible at customer relations, but he is a great guy.

Be yourself. Don’t alter yourself so others like you.