In the very first episode of Showtime’s popular comedy-drama series Shameless, viewers got to see Fiona Gallagher meet and quickly fall for Steve Wilton, an attractive and seemingly successful man who had tried to stop a thief from stealing her purse. Fiona spent most of her life raising her younger siblings in a crowded and chaotic household, so Steve’s willingness to put her needs first for a change and his incredible generosity made it seem like he was just what she needed.
Over time, Steve revealed that his name was actually Jimmy Lishman and that his fortune was actually amassed by stealing cars. Jimmy and Fiona’s relationship quickly became rocky as Jimmy’s lies continued to stack up and Fiona’s familial issues kept her from focusing on her romantic life. Since Ian Gallagher’s character earned a relatively happy ending with his Season 1 boyfriend Mickey Milkovich, countless fans hoped Fiona would similarly end up with Jimmy before Emmy Rossum left Shameless in Season 9 regardless of the fact that the two were always far from perfect.
Updated on August 31st, 2022 by Tanner Fox: Jimmy and Fiona were never good for each other, but they couldn’t seem to say out of one another’s lives. When Jimmy returned from Chicago, Fiona sacrificed a healthy, functional marriage just to be with him, and it dragged her into yet another bout of romantic chaos.
Had the two been communicative and openly appreciative of one another, their relationships may have been less rocky. However, Jimmy was a habitual liar, and Fiona often came across as uncaring. Plenty of fans were pulling for them, but, ultimately, as a couple, they didn’t make all that much sense.
Jimmy’s Hypocritical Introduction
Jimmy proves that there really isn’t any honor among thieves; while watching Fiona Gallagher dance at a nightclub, he saw her purse get stolen, and he immediately chased after the robber. He was unsuccessful in his attempt to stop the criminal, but Jimmy was made out to be a hero for trying, and his momentary nobility helped him slide into Fiona’s life and heart.
Unfortunately, Jimmy wasn’t quite the knight in shining armor that he was initially made out to be. He was a professional thief himself, and, instead of stealing purses, he actually made a living stealing cars. Jimmy did seem to truly love Fiona and want to help the Gallagher family, but, at the end of the day, he was just another criminal who threatened to make their already chaotic lives even more complicated.
Fiona Encouraged Jimmy’s Criminal Career
Fiona has never been able to maintain a healthy relationship with someone who was actually right for her and good for her family. Mike Pratt was great with her siblings, had a stable job, and was exceptionally friendly, but she ruined her relationship with Mike by being with his manipulative brother. Her marriage with Gus was going well right up until she had a brief one night with Jimmy. She nearly married Sean even though she knew he was a former addict with a criminal history.
Fiona’s trend of making bad relationship decisions all started with Jimmy Lishman. She wasn’t attracted to him when she thought he was a wealthy businessman, but, as soon as he revealed that he makes a living stealing cars, she suddenly wanted to be with him. When he decided to give that life up to become a doctor, they broke up.
Jimmy Gave Away The House He Bought Fiona
Jimmy wasn’t afraid to blow all of his hard-earned car theft money to make Fiona happy. He bought her everything she needed to make life in the Gallagher house easier, and, when that still wasn’t enough to satisfy his girlfriend, he spontaneously bought the house next door so she could finally have a bit of freedom and privacy from her siblings. It was an incredibly romantic and thoughtful gesture, but the house sadly didn’t stay in his and Fiona’s possession for very long.
In an attempt to keep Tony Markovich from arresting him for grand theft auto, Jimmy simply gave the house to his rival for Fiona’s heart. Tony already said he wouldn’t turn Jimmy in if he just left town, so this was an illogical move that stripped Fiona of a gift he had promised her.
Fiona Couldn’t Make Up Her Mind About Jimmy
Most people in healthy relationships never debate if they should be together. Fans seem to think that Jimmy is Fiona’s soulmate, but Fiona herself has never been sure about Jimmy.
When Jimmy returned to Chicago after fleeing the city in the first season, Fiona was torn on whether or not she should give him a second chance. She messed around with him in a bathroom while she was on a date with another guy, but she immediately regretted it and led him on for weeks. When she was married to Gus, she slept with Jimmy as soon as he came back to town, but they broke up shortly after.
Jimmy Took Lip In Just To Upset Fiona
When Jimmy came back to Chicago, he immediately tried to get Fiona back. She initially refused to resume their relationship because Jimmy was now married to Estefania and she still didn’t forgive him for leaving her in the first place, so Jimmy had to utilize some sketchy tactics to slide his way back into Fiona’s life.
Jimmy tried to help out around the Gallagher house and drive Fiona’s siblings around town in the hopes that Fiona would become reliant on him and decide that she needed him. When that didn’t work, he let Lip stay at his apartment after Fiona kicked him out for dropping out of high school, knowing that this would anger Fiona and force her to finally have a conversation with him. Good boyfriends don’t have to resort to this level of emotional manipulation.
Even The Writers Struggled To Bring Them Back Together
Jimmy’s attempts to get back with Fiona upon returning to Chicago didn’t quite work out, so the Shameless writers had to come up with somewhat nonsensical ways to force the former couple to interact. That’s when Fiona’s friend Jasmine invited both Jimmy and his new wife Estefania to a party she was hosting on a fling’s boat.
There are countless reasons why this didn’t make any sense. Jasmine knew that Jimmy broke Fiona’s heart when he first left town, knew that Jimmy was now married, and knew that her best friend didn’t want to see him. Jasmine also had a secret crush on Fiona and kissed her at that same party. She explained that she contacted Jimmy about the party to try to get them back together, but, if Jasmine cared about Fiona or wanted to be with her, she shouldn’t have invited him.
Fiona Barely Cared About What Jimmy Was Up To
When Jimmy first revealed to Fiona that he made all of his money stealing cars, she never really expressed any sort of concern that her boyfriend would get caught one day and find himself behind bars. She was too busy worrying about her siblings and problematic father to really worry about Jimmy or keep tabs on what he was up to.
When she came across Jimmy burning his own clothes in front of the Gallagher house late one evening, she didn’t even think to question why he was doing that. He had just been forced to do endure something awful and looked traumatized as he set fire to his clothes, but Fiona was too focused on other things to notice or ask if he was okay.
Jimmy Was Never Honest About Estefania
Jimmy’s marriage to Estefania was a complete sham; a criminal had forced Jimmy to marry his daughter so that she could legally live in the US, and he repeatedly threatened to end Jimmy’s life if he didn’t keep up the charade and make their relationship seem real to government officials.
For some reason, Jimmy wasn’t open about the reasoning for his marriage to Estefania with Fiona even after they finally started dating again. Fiona had no clue how much danger Jimmy was in from Estefania’s father Nando and his henchmen, so, when he disappeared for the second time after being forced onto Nando’s boat, it was a complete shock.
Fiona Only Cares About Her Own Problems
As the primary guardian of all of her siblings, Fiona always had a lot on her plate, and she didn’t have much available free time to spend talking to Jimmy or helping him solve his issues the way he constantly consoled and helped her. Jimmy never really expressed any emotions about this neglect until he found out his father was divorcing his mother and was having an affair with Ian Gallagher.
Jimmy desperately wanted to talk to his girlfriend about this surprising revelation, but she was too focused on her own family drama to spend even a few minutes discussing Jimmy’s father’s issues with him. Jimmy then finally called Fiona out on her selfishness, and this started a fight that they never truly resolved.
Their Fights Left Deep Scars
All couples have their disagreements, but healthy couples definitely don’t react to arguments as poorly as Jimmy always seemed to react to fights with Fiona. When he yelled at Fiona for always only caring about her own problems and never reserving any time to talk about his, Jimmy just tried to pretend the fight never happened, and the couple moved on without resolving this glaring issue. When he got especially angry, he chose to get revenge on Fiona by being with another woman.
Jimmy and Estefania were only together on paper, but, whenever he and Fiona had issues, he messed around with his wife to release some of his stress and anger. He always maintained that he solely loved Fiona and expressed some remorse for his infidelity, but, if he truly cared about her, he wouldn’t have done that in the first place.
They Didn’t Make Plans For Their Future Together
Before Jimmy was forced to leave Fiona for the second time, he considered putting an end to his life of crime and going back to medical school in Michigan. He asked Fiona if she and the other Gallaghers would like to leave Chicago with him, but Fiona soon found out that he submitted an application for a studio apartment. He never actually wanted Fiona’s siblings to come along and join them in their fresh start.
Fiona was happy for Jimmy when he revealed his plans to get his life back in order, but, once she discovered the truth about his desire to take Fiona away from her family, they got into a huge fight. Fiona pointed out that they never made decisions together, and Jimmy was unable to argue against that fact.
The second time Jimmy reappeared in Chicago after months of no contact with Fiona, he decided against immediately approaching her and begging her to take him back. Instead, he asked his mysterious friend Angela to spy on Fiona for him to see whether or not she was happy or entered into a new relationship. Angela repeatedly appeared at Fiona’s restaurant to keep tabs on her until Jimmy finally decided to reveal that he was back.
Jimmy never really explained why he waited so long to approach Fiona or why he continued to pursue her after he found out she was married to Gus. If he really cared about her, he would have just stayed out of her life upon discovering that she was finally moving on and in a good place in life.
They Never Sorted Out Their Issues
Throughout Fiona and Jimmy’s on-again-off-again relationship, they expressed a variety of issues with each other that were never properly amended. Fiona was absolutely right that Jimmy failed to include her when making big decisions, and Jimmy was right that Fiona only seemed to care about her own problems and couldn’t be there for him when he wanted to vent about his father.
They always seemed to get right back together after major arguments, but none of the problems that were brought up during their major arguments ever got resolved. Good couples are able to forgive and forget their partners’ minor indiscretions and failings, but they don’t just ignore glaring issues in their relationships the way Fiona and Jimmy always do.
Fiona Sacrificed A Healthy Marriage For Jimmy
Shameless fans were surprised when Fiona damaged her amazing relationship with Mike Pratt beyond repair to sneak around with his rebellious and manipulative brother Robbie, but that wasn’t the last time she’d sabotage her own love life. A few years later, she spontaneously married Gus Pfender, and the two of them seemed to be very happy together until Fiona decided to be with Jimmy again.
Jimmy had already broken Fiona’s heart and abandoned her without warning twice, but, whenever he came back to town, Fiona just couldn’t help but jump right back into bed with him. She immediately regretted cheating on Gus and told Jimmy that she wanted to be with her new husband, but the damage was done, and Fiona found herself alone once again.
Jimmy Constantly Lies To Fiona
Jimmy has lied to Fiona ever since their very first meeting; he introduced himself as Steve and let Fiona believe he was a successful businessman when he was really a car thief. Later in the relationship, he hid the truth about his dealings with Estefania’s drug lord father from Fiona for reasons unknown. When he returned to Chicago several months later, he had taken on yet another new identity, and his friend Angela knew him as “Jack.”
Jimmy seems to be a habitual liar, as he also let his family believe he was away at medical school when he was actually back in Chicago stealing cars. There’s really no reason to believe he’ll ever change.
He Expected Debbie To Life To Fiona For Him
When Debbie Gallagher saw a suggestive text on Steve’s phone from another woman, she took it upon herself to investigate and see if her sister’s boyfriend had a secret second relationship. Her sleuthing took her to Candace Lishman’s home where she found out that Steve was actually Jimmy Lishman, Candace’s son.
Candace had no clue that Jimmy had taken up a new identity and was living in Chicago. When Jimmy walked into his childhood home and found Debbie there waiting for him, he immediately begged her not to tell Fiona who he really was. For weeks, he forced Debbie to lie to her own sister and gave her gifts in exchange for her silence.
They Never Treat Each Other Like Partners
It’s important for couples to treat each other with respect; partners are supposed to run financial decisions by each other, even when one individual in a relationship makes more money than the other. They’re supposed to make plans for the future together, and they’re supposed to be there for each other during both the good times and the bad.
Jimmy and Fiona may have been a fun couple to watch, but they never treated each other like true partners. Jimmy always bought whatever he thought Fiona needed without asking her first. He applied for a studio apartment in Michigan before asking Fiona if she’d leave her brothers and sister to be with him. When Jimmy finally needed Fiona to support him emotionally the way he was always there for her, she failed to do so.
Fiona Was Never Appreciative
Fiona always claimed that she was able to handle taking care of herself and her siblings all on her own, but, deep down, she really enjoyed the way Jimmy constantly pampered and provided for her. She eventually accepted the washing machine he gifted her after their first night together, she never turned down Jimmy’s offers to help out around the house, and she was more than happy to accept the house he gave her. Yet, for some reason, she never properly thanked Jimmy for his constant generosity.
Thanking Jimmy would have required Fiona to admit that she could use some help, and Fiona always refuses to rely on anyone other than herself. So, she opted to seem unappreciative whenever Jimmy did something to try to make her happy.
Fiona Only Reached Her Potential Once Jimmy Was Gone
In more recent seasons of Shameless, Fiona finally started to get her life together. She made a big gamble buying an old laundromat, but she quickly made a significant profit on that purchase and was able to use the money she made to buy an entire apartment building.
After years of struggling to find a good job or way to support her family, Fiona got her life on track. That never would have happened if she was still with Jimmy because Jimmy’s constant pampering kept her from having the drive to hustle to make money. Without Jimmy in her life, Fiona was forced to push herself to her potential. She just seems to be at her best when he’s not in the picture.
Jimmy Was Always Indecisive
Jimmy Lishman just never seems to figure out what he wants; he resented his parents’ dream of him becoming a wealthy and successful doctor, but he asked Fiona to move with him to Michigan so he could go back to medical school. He loved the chaos of the Gallagher house and enjoyed providing for Fiona and her siblings, but, in a moment of anger, he called her home a slum and implied that he deserved better. When he returned to Chicago for a second time to win Fiona back, he spied on her for weeks before announcing his arrival.
Outside of knowing that he wants to be with Fiona, Jimmy doesn’t know much else about his future or what roads he wants to take in life. Even if he and Fiona are meant to be together, they have a lot of self-exploration to do before they can enter into a healthy, stable relationship.