From HOTHIPHOPDETROIT. com – Word has it that Diggy Simmons has been secretly engaged since Christmas to his girlfriend Jessica Jerrell. The wedding is said to take place when young Diggy turns 18 exactly one year from today (His Birthday is March 21, 1995). One thing for sure, Ms. future Diggy just hit the jackpot that’s money on top of money old money and new money lol…you go girl!!