Jon Arbuckle has gone on dates with numerous women. Prior to July 2006, he had little luck with romance.
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Abigail was a woman that Jon went out on a date with. As with many of Jon's dates, his date with Abigail was a disaster, as he came home at 8:45 (he had left at 8:00), to which Garfield was not surprised.
Cactus Jackie (voiced by Louise DuArt) was Cactus Jake's only daughter. She told Jon during a dinner date (joined by Cactus Jackie's family and Garfield) that she only dates cowboys. Jon tries to impress her, only to fail at doing so. Garfield then tries to help Jon by using Cactus Jackie's horse and some adhesive pasta that he got from the restaurant.
Christy Comely was a supermodel whom Jon saw on a magazine cover, wishing he could meet her and get a date. No sooner then he said that, his phone rang and his wish came true when Christy called him. However, it is unknown whether or not they went out on the date because as Jon was getting ready, he sang he wish he was in Dixieland, then his wish came true. Later, he wishes he was home in bed. Then his wish came true. This made him scream and hide under the covers.
Cynthia Underberger was one of Jon's dates Garfield went over in one episode.
Cynthia tolerated him buttering his arm instead of his biscuit. She excused his attempt to order dinner in French, causing the waiter to serve them two soft-boiled athletic shoes. She also forgave him for forgetting his wallet, forcing them to spend the night washing dishes to pay the check. Originally, they had to wash 747 dishes to pay for their meal (due to some of the dishes breaking, it became 748 dishes, their waiter's car, and every other car in the lot). The next morning, Cynthia joined the marines, sailed to Greenland, and has not been seen since.
Diana (voiced by Julie Payne) was a woman who came to Jon's house in an attempt to sell him insurance.
Jon, having met her in a park, invited Diana to his house for a date. He was unaware that she was just an insurance saleswoman trying to get him to buy a policy. After some of Garfield and Odie's shenanigans, she gave up and left the house immediately.
Frieda was a woman Jon went out with. But like many of his other dates, it was a disaster, since he was only gone for twenty minutes, only to find a burglar in his house, which made him call the police.
Lorelei (voiced by Susan Silo) was a woman who went out on a date with Jon in the episode Bride And Broom (Garfield and Friends). Unlike many of the other dates Jon has been on, this went on till after dinner (much to Jon's surprise). However, what Jon didn't know at first was that Lorelei was really a witch in disguise, and she wanted to marry him, even though he wasn't ready (Lorelei's boyfriend Cecil was the same way).
Marian (spelled Maryanne in the subtitles; voiced by Susan Silo) was a woman whom Jon took on a canoe ride for a date. She claimed that Jon was a wonderful singer and that she enjoyed his company, but when Garfield broadcast her thoughts, she is really annoyed at everything Jon is doing and would rather be doing anything else. Eventually fed up with Jon, she jumps out of the canoe and swims out to shore.
Marsha (voiced by June Foray) was a woman Jon dated after he had gotten a sentient car. During her date with Jon, she was annoyed and insulted when she thought Jon had insulted her (unaware that it was Jon's talking car who had done so). This made her abandon the date.
Rosalyn (voiced by Desirée Goyette) was a woman whom Jon met on a plane to New York. The two later go to an Italian restaurant, with Garfield secretly following. It is there that Garfield learns that Rosalyn is a pickpocket who just wants to steal Jon's wallet. She is eventually arrested by an agent from the Federal Bureau of Picketpockets Prevention, who also gives Jon his wallet back.
Sometime during the date, Jon accidentally spilled a plate of linguini on Selma's head. After that, they left the restaurant. Jon apologizes for what happened, but Selma just tells him that she never wants to see him again. She then goes to the marine recruiting office across the street from the restaurant and practically begs one of the workers there to send her to a foreign country.
Sylvia Finster was one of Jon's dates described by Garfield in one episode.
She held the world record for the shortest date with him. Jon had picked up Sylvia, wanting to talk a little bit about himself. Two seconds later, Jon turned back to Sylvia's house, sadly thanking her for a lovely evening. Sylvia runs screaming back to her house.
Zelda Zeekly was a woman who went on one date with Jon. He called her, telling her that the one evening they had spent together was one of the most memorable of his life. But Zelda doesn't remember him, until she remembered that Jon had a cat. She has been hiding from Jon. When Jon asked if she was busy that night, she said yes. In fact, when Jon asked how far ahead she was booked, she said up until the turn of the century. Jon then told her to have a nice decade and hung up.
One woman's dinner date with Jon is shown as part of Annoying Things. She became annoyed by things Jon had told her. Finally, when Jon tried to kiss her, she dumped her pasta dinner on Jon's head and left the restaurant.
One woman (voiced by Sharman DiVono) whom Jon met at a ski lodge became interested in Jon when he claimed to be good at skiing (after the ski lift became broken). He fabricates a story of his life skiing up until he hears that the lift has been fixed. He then becomes almost a nervous wreck when he now has to prove he's a good skier. She made a cameo in the episode, Jumping Jon.
A woman (voiced by Desiree Goyette) came to Jon's house after Diana had left. She was the roofer who was supposed to be at Jon's house sooner to fix some leaks in his roof, but she was busy with other leaks. When she came to Jon's house, she asked if he was the same guy who drew the cartoons, to which he says yes, seemingly surprised. He asks the woman if he can get her anything, to which she asks him if he has any hot cocoa (she loves hot cocoa).
One woman (voiced by Louise DuArt), after arriving to Jon's house by mistake when she came to the wrong street, decided to go on a date with Jon after finding out he was a cartoonist, and furthermore after seeing his music record collection, despite not being familiar with the music format.
Ten women have gone on dates with Jon, each shown flashbacks as Garfield explains the top ten reasons why dates with Jon are always so short.
The first reason (or #10 since Garfield counted backwards) was most women don't appreciate a dinner where a teenager asks "you want fries with that." The second reason was that women like being serenaded, but not in the middle of the movie (Jon started playing his accordion and singing, annoying the customers and embarrassing his date). The third reason was pasta not meant for external use (Jon spilled his pasta on his date's head). The fourth reason was that the romantic mood was spoiled by the phrase "you may have to get out and push" (Jon's car broke down and Jon made his date push his car out in the rain, to which he told her "keep going. It's almost starting"). The fifth reason was Jon did an impression of a monkey swinging, embarrassing his date. The sixth reason was that most women prefer adjoining seats at a concert (Garfield came along). The seventh reason was Jon gave his date a Venus flytrap as a corsage (the man at the florist shop said she'd love it), and it almost ate her alive. The eighth reason was that Jon forgot to double check if it really was a costume party (he was dressed as a chicken, and the only one in a costume). The ninth reason was that Jon told his date about winning his high school dodgeball championship, which was really boring. The tenth and last reason was that sometimes Jon shows up without his pants on.