18. Kristin Davis – Jenna
While dropping someone’s toothbrush into a toilet may be a bone of contention for some, it’s grounds for divorce for Jerry. Indeed, throughout season eight’s “The Pothole,” the comedian became so obsessed with girlfriend Jenna using a soiled brush that he called off their relationship. Thankfully, though, actress Kristin Davis landed less icky parts later in her career – most notably as Sex and the City’s Charlotte.
17. Teri Hatcher – Sidra
Jerry becomes so insecure about the supposedly fake breasts of girlfriend Sidra – played by Teri Hatcher – that she dumps him at the end of season four’s “The Implant.” Of course, years later, Hatcher would continue to flaunt her “real” and “spectacular” figure through hit show Desperate Housewives.
16. Marcia Cross – Sara
In addition to Teri Hatcher, Jerry also dated future Desperate Housewives star Marcia Cross in season nine’s “The Slicer.” In it, the flame-haired actress plays dermatologist Sara, whose claims of being a doctor begin to get under Jerry’s skin. That is until he learns about her work with cancer patients, which leads to one of the show’s most embarrassing and awkward moments.