How to squeeze a pimple or zit
There are two schools of thought about pimple squeezing or pimple popping or squeezing zits or popping zits.

  One school of thought is don't do it, the other is go ahead. Personally I can't advocate either one or the other as I have perfect skin and never have had the problem of pimples.
Most rational people, such as parents, would advocate using medication so as to avoid scarring.
But!

  To pop a pimple more safely steam your face. That will loosen the junk in your pores and help to slough off dead skin. It opens your pores and makes your skin softer, then you can clean your skin easier. Never actually use hot steam right on your face as you could burn yourself. Use a face towel with water as warm as you are comfortable with or put your face over a sink of warm water and let the vapors rise onto your visage. The longer the better to a point. After a shower your skin is already softer so that is a good time to do it. You do want to really soften the skin but not so much as to allow the skin to fall off your face.  (You would look ugly with no face just bones and ligaments etc...)
  
   You should squeeze the softened area around the pimple gently until it bursts forth with excreta. It is important to have clean hands and everything that you use should be clean so as not to introduce germs and disease into your skin. Remember that you can scar your face if you are too forceful or if the pimple isn't really "ripe".  Stop if clear fluid or blood comes out. If the pimple doesn't seem to have a white cream filled center then it isn't ready for popping. At that point you would do damage to your skin. Then you would look really ugly and you wouldn't have any friends, and possibly never find a mate. People would call you scarface behind your back and say other awful things about you. So, think before you do it.

  
   A person should never squeeze a pimple in someone else's general direction as that can spread germs and filth. I have heard that a dab of alcohol on the pimple will help dry it out and kill germs are popping. If I had the problem my alcohol of choice would be Jim Beam but I think from hearsay that you should use that medicated rubbing alcohol. Don't get it into your eyes.
  
   It is a good idea to use medicated skin cream. The clay mask a couple of times a week is also a winner. It really does help to remove excess oil and firm the skin, although you will look like a tard with it on so no pink pajama parties with the clay mask. Do you hear me guys?.

  Don't pop pimples with fingernails, they almost always have germs hiding under them. Use a kleenex wrapped around your index fingers.

  Now blackheads! That'is another subject altogether. I saw a girl with blackheads that were really big once and I puked...on her. It could happen to you, so don't think even for a minute that people don't notice. They are doing their best to keep their lunch down while they look at you. At that point they have already decided that they would rather mate with a goat than get romantic with you. Don't be a disgusting pig!  You know who you are! If you have the black pustules from hell on your mug go and wash your face!... Do it now!! Right Now! Go and do it!............... Disgusting Pig.

Further reading  Pick Your Nose