To date or be in a romantic relationship. In Chile, this term covers everything from a brand new romance to a serious long-term commitment. (Chileans use the related terms pololo or polola for boyfriend and girlfriend to distinguish them from a fiancé).
Claudio is so in love that he asked Martina to pololear in front of all their friends.
To start a formal romantic relationship or become an official couple. It refers to the act of being in a steady, committed relationship as boyfriends or girlfriends. (Although listed here for Mexico, this term is the standard word for dating in Chile).
It is great that you two finally decided to pololear, it is obvious you really like each other a lot.
To be in a committed, official romantic relationship without being married. It is the standard Chilean term for dating or having a boyfriend or girlfriend (Chileans typically use the word 'novios' only for engaged couples).
Hey, did you hear that Nacho finally started to pololear with his best friend's sister?
To be in an official relationship as boyfriend and girlfriend. It is not just casually dating: it implies a formal commitment where one person has explicitly asked the other to be their partner. (This term is primarily used in Chile).
Guy: Do you want to pololear with me? Girl: No! Guy: U.U Girl: I was just kidding, I love you! Guy: Me too and other crazy shit!
To woo or flirt with someone using sweet talk and charm to win them over. It refers to the initial phase of trying to attract someone you like (in Chile, a pololo or polola is a boyfriend or girlfriend).
Nacho spent the whole party pololeando the new girl to see if he could get her to go out with him.
To be in a committed relationship or date someone exclusively. It describes the stage where a couple is officially together (in Chile, this term is the standard way to say someone is your boyfriend or girlfriend, whereas the word novio usually implies being engaged).
We have been pololeando for almost a year and we have already met each other's families.