Complex sentence: She has been engaged to a congressman (when she was 16 years old) and to David Blaine, and she dated O. J. Simpson, a music producer (hinted at having been RedOne), a sniper, and a mob boss.
Split into simpler sentences: She has been engaged to a congressman (when she was 16 years old) and to David Blaine. Dated a sniper (who threatened to kill her but was just bluffing because he couldn't face his mother let alone kill someone), O. J. Simpson, a music producer (hinted at having been RedOne), a sniper, and a mob boss.