It went off the rails when Private Parts got serious. that would have been around late 96. Howie’s ego went into overdrive. It was already bad enough earlier in 95 when john Avildsen was having dinner at casa Stern... but when ink was actually on the deal and a heavy hitter like Ivan Reitman came in, Howie couldn’t handle it. Superstars can’t be married.
By 97 Howard was intolerable and was probably already cheating. The condoms incident was just Howard trying to lie and pretend but he totally got caught.
’98 he moved out into the city, which was documented on the show, marriage was already over by then.
his “wild tear” actually took place in the summer of 98. he met beth earlier than either one of them has admitted to because Howard’s divorce wasn’t finalized at the time, but my guess is summer ’99.
Angie Everhart, Robin Givens etc might have overlapped the Beth relationship but that was either a) image management and it never happened or b) he and Beth simply weren’t exclusive until 2000