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"
by Quelmo Rodriquez June 18, 2010
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