Uneeq, I have some news for you. No one speaks Yiddish to create machloikes. We speak it to keep our old world alive in the new world and we are very happy when someone wants to learn it.
Most Yiddish speakers would be very happy if you asked them to help you understand Yiddish. No one except the occasional bad apple you might encounter in any bunch is looking to divide or to be condescending. If anything some Yiddish speakers would love to have one more person to pass the language on to.
Start by following along with the lyrics as you listen to a Lipa Schmeltzer song like Gelt, unless you davka want to learn only Litvish Yiddish – in that case get the old Avraham Fried Yiddishe Oitzros albums with the lyric books. If you want to hear what people in the street are saying, Lipa-lushen is best because today, mostly Hungarian and Polish Chassidim speak Yiddish on a daily basis. Lipa’s Americanized Yiddish is only a slight exaggeration of the way people speak today; Michoel Schnitzler and Yonason Schvartz sing very clearly as well and I would say they are singing in exactly the same Yiddish most people speak today.
Once you feel ready, find a shiur given in Yiddish and you will catch on very fast. Usually, you find someone who davka wants to help you keep up with the shiur and that person will help you if you even look puzzled when the magid shiur is speaking.
The Chumash Beis Yehuda helps you learn to read Yiddish.
And then, you can tell the occasional condescending menivel “Shygetz Aross” (or is that really Hungarian? :)))