1) To engage in risky behaviour;
2) To be venturesome;
3) To be wildly promiscuous;
4) Or, to be silly to the point of the ridiculous.
"Stop driving like a Flippin' Raymond!"; "The girls came back to ours; we acted like Flippin' Raymond's!"; "I saw them pissed up on Broad Street, chasing each other around like Flippin' Raymonds"