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However, the proposal was nearly jeopardized when Jenny learned that Ryan hadn't been playing darts with Esposito the night before (he had been going to visit her parents for their permission), matters being made worse when Jenny learned that Natalie Rhodes was currently working with the team (Natalie was one of Ryan's 'Five Freebies' of celebrities, being one of five women Ryan could sleep with if he ever got the chance).However, she eventually came back to the precinct to accept Ryan's apology, prompting Ryan to propose to her right there in the station, the two being warmly congratulated by Ryan's colleagues.(Under Fire) According to Ryan in Montreal, Jenny lost her job and the two have been scraping by with the baby expenses, including taking care of Sarah Grace.She did appear as her husband's guest in Hollander’s Woods Ryan stated that Jenny is pregnant again with their second child, which makes their daughter a big sister.During an investigation it was discovered that the victim - a pick-up artist - had sex with Jenny while she was dating Ryan, but Ryan clarified that at the time of the 'affair' he and Jenny had not agreed to be exclusive to each other.

("The Wild Rover") Ryan was trying to be prepared since Jenny was 5 months pregnant and they only have 4 months to go before the baby arrives.Although Esposito and Castle expressed doubt over Jenny's existence, she was subsequently confirmed to be real when she visited Ryan at the precinct, commenting that she felt that she knew Ryan's colleagues after hearing all of his stories about them ("The Mistress Always Spanks Twice").When planning to propose to Jenny, Ryan asked Castle for advice and arranged a helicopter flight over some of their most memorable locations - including the bar where they met intending to finish it off by eating in an Italian restaurant that Castle recommended near their heliport.In Secret Santa, the couple was putting up the tree and Jenny told Ryan, "It just doesn't feel like Christmas without kids.", stating that she wants to start a family.In Reality Star Struck, she made her husband arrive late for work sweaty, somewhat poorly dressed and left for any time to try making a baby, due to the fact that her temperature spike up and she's sexually ovulating.