Episode 363 is Red Shoe Diaries (1992)

Jake yearns to understand the secret life of his late fiancee. To find the answer, he solicits the most heartfelt, passionate, and intimate entries in other women's diaries.

"Safe Sex"

A woman looking for release from the pressuring job finds a man looking for the same thing. Protection and no names are the rules of the Tuesday and Thursday affair. The woman puts spice into the affair as well as the man until the woman snoops through the man's mail and finds his name breaking the rules. The affair is broken off until they re-unite weeks later and start over again with a normal relationship.