Despite his reputation with women, Jim did not have that many relationships during his time in the show.<ref name="Monroe"/> Dale complained about this, stating thatas he thought Jim's celibacy was unrealistic.<ref name="Monroe"/> Shortly after ''Neighbours'' began, Jim has a brief relationship with [[Maria Ramsay]]'s ([[Dasha Bláhová]]) sister [[Anna Rossi]] ([[Roslyn Gentle]]), who leaves him because she does not want to cause a feud between his family and the Ramsays.<ref name="Monroe2">[[#refmonroe2|Monroe 1994]], p.100.</ref> Jim's next romance is with [[Zoe Davis]] ([[Ally Fowler]]), which shocks the neighbourhood because she is twenty years his junior. Dale did not think there was anything wrong with an older man dating a younger woman.<ref>[[#reforam|Oram 1988]], p.109.</ref> The relationship does not sit well with the Robinsons and Lucy is especially unhappy about it. However, Jim and Zoe continue to date and are shocked when Zoe becomes pregnant.<ref name="Zoe">[[#refmonroe2|Monroe 1994]], p.134.</ref> Jim is reluctant to become a father again in mid-forties and he and Zoe grow distant, as she wants to keep the baby.<ref name="Zoe"/> Jim later proposes to Zoe, but when she suffers an [[ectopic pregnancy]], they break up.<ref name="Zoe"/>
Later that year, Jim meets Englishwoman [[List of Neighbours characters (1986)#Ruth Wilson|Ruth Wilson]] (Stephanie Daniel) on a plane, while he is returning home from the United States.<ref name="Ruth">[[#refmonroe2|Monroe 1994]], p.101.</ref> The couple "got on like a house on fire."<ref name="Ruth"/> Ruth checks into Lassiter's Hotel, which is run by Paul. However, when Ruth is unable to pay the bill, Jim steps in and pays it for her. He then invites her to stay with his family for the duration of her visit to Australia.<ref name="Ruth"/>
