Sing and Play

I could use some tips on playing and sing at the same time. How do you do it? What are some songs that are good to start with?

Well, i would start off with singing to some simple 4 chord songs. Then probably go to some songs like "smells like teen spririt, where you have some muted strikes or, weird rhythms. Then go to some fingerpicking and singing along (Green Days "Good riddance" is an example, or "Dust in the Wind") And when you finally can sing to some crazy guitar parts like the guitarist of The Fall of Troy, then you are just mad, haha.

I would start by playing a song you really have down, then pausing between strums or picking to sing. Then start overlapping a little, then a little more.

Try 'Hey Joe'. It's easy and happens to be a circle of fifths to boot.
Well maybe not a circle of fifths, but the chords are fifths apart.

The method I used when I was first learning was to start simple with a couple of chords and hum the root note of each chord as it is played. once you have this down try humming a simple melody in the corresponding scale. this will also help you to develop your ear.

it takes a little time but i think this will help

What I did was first learn to play without looking down. Then I would quietly sing to myself and gradually work up.
I started with Green Day's Holiday, and Basket Case.

Another good place to start is backing vocals. Then gradually extend to whole lyrical pieces.

Thank you everyone you have been a big help. Good to know I'm on the right path.