You can't make this stuff up! The dashing Michael Lenoci joins Blaine to figure out the dating life of Boss Lady Shannon + we have the CRAZIEST MATCHMAKING MOMENT IN THE HISTORY OF PODCASTING!! Plus, what is Shannon's upper age limit? Why do all her exes have Peter Pan Syndrome? Would you date a man who makes less money than you? Should you Facetime before the date? And is it okay to give dating ultimatums??See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.