what does 'pip you' mean?
Like, count it against you, or consider it a black mark.

Oh. I guess that term hasn't made it to or into common use in Socal/on the west coast. I've never heard anybody use that before! Is it an east coast or mid west thing, kinda like in some states everybody refers to soda as 'pop' and instead of saying 'grab me a coke' they say 'can you grab me a pop while you're in the kitchen'? I learned that one in a fast food drive-thru when in the midwest for my brothers wedding. I placed my order for a meal deal combo that included a drink and the girl asked "and your pop?", I was confused (but thinking Wow, cool friendly family type town!) and said he was back at the hotel eating room service and didn't want anything, then she asked again 'what kind of pop you want with your burger combo?'
As to your question, no LS's don't pip you for not having work experience in the legal field. Work experience in a law office and/or as a paralegal does not impress them or give you an application edge. LS's generally like students that don't think they already know the law, how it works, how to be a lawyer, etc. They want you to be the student and learn the law and how it works from them since you are applying to be a student at their school.
It doesn't hurt to have WE in a law office or other legal type of job on your resume, but it doesn't add big bonus points to your admission chances because it was in a legal realm and you worked with lawyers.
LS's seek to put together a diverse set of people with diverse backgrounds and experiences for each incoming class, so any good/interesting non-legal work experience that demonstrates the qualities LS's seek in students and that makes you diverse/unique/interesting in some way is good for your application.
PS: I'm going to try using pip in conversation with some friends and people around the town to see if they get it!

Would it be proper use to say in conversation to a friend, say if we were hanging out at a bar, "After I said hi, introduced myself, and bought her a drink we talked for a few minutes and she seemed into me. IDK what happened, I thought she would give me her number but then her friend showed up and pip'd me, then they both walked away" ?