It seems like you're really just trying to ignore the fact that HE HAS CHEATED ON YOU AND LIED TO YOU. If that in itself isn't bad enough, he has also told you he's a PICK-UP ARTIST. Next, ALL OF HIS FRIENDS ARE THE SAME. Any one of these is already a huge red flag, and yet he encompasses all of these extremely negative qualities. You're really just setting yourself up.
To summarize, YES, HE WILL CHEAT ON YOU AGAIN, even if he promises he won't.