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Shameless: 20 Things That Don't Make Sense About Lip's Relationships

None of the members of Shameless' Gallagher family seem capable of maintaining healthy relationships with people who are actually good for them. Frank and Monica's relationship was never functional, so the Gallagher children didn't have positive role models growing up to teach them about love. Fiona repeatedly finds herself abandoning stable and sweet guys for more rebellious and manipulative options, Carl was practically forced to get married long before he was ready, Ian's happy ending with his supposed soulmate is going to take place behind bars, and Debbie tricked her crush into getting her pregnant.

Lip's heightened intelligence should help him recognize the failings of his siblings and keep him from going through the same relationship issues that they've experienced over the years, yet he often finds himself dealing with more dating troubles than anyone else in his family.

Every time things start going right for Lip in Shameless, one of his relationships implodes and sends him on a downward spiral which keeps him from reaching his potential. Even though he's been dealing with problematic girlfriends ever since he started dating Karen Jackson in the series' first season, Lip clearly hasn't learned his lesson and continues to seek out partners who he knows aren't right for him. He's supposed to be the Gallagher with the brightest future, but Lip is always willing to sacrifice his jobs, friendships, family relationships, and education to be with his latest dysfunctional crush.

Here are 20 Things That Don't Make Sense About Lip's Relationships. 

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Lip Gallagher and Karen Shameless
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20 HE KNEW KAREN WASN'T GF MATERIAL

Lip Gallagher and Karen Shameless

Karen Jackson was never subtle about how open she was to experiment with anyone who was willing to be with her. When Lip asked her to help Ian figure out whether or not he liked being with girls, Karen didn't care that she and Ian had just met and was eager to be his test subject. Yet, when Lip and Karen' s relationship started getting serious, Lip seemed to be surprised by how promiscuous she was.

Lip found himself put off by how many guys Karen had been with, and was extremely hurt when Karen revealed that he wasn't the only person who could be the father of her baby. Lip was right to be upset that Karen didn't remain faithful to him when they started developing real feelings for each other, but he shouldn't have been particularly surprised, either.

19 HE BLAMED FRANK FOR BEING WITH KAREN

Lip and Frank Gallagher Shameless

When Lip found out that Frank had been with Karen, he attacked his father and blamed him entirely for the occurrence. Frank was a fairly awful person and couldn't really be trusted to deny himself of any pleasure, but he wasn't the type of man who'd willingly be with the underage daughter of the woman who was letting him sleep under her roof.

Karen tricked Frank into being with her when he was too intoxicated to resist, just so she could get revenge on her own father. She was a very impulsive and manipulative teenager, so this wasn't out of character for her at all. Yet Lip didn't even consider the possibility that Karen was behind everything and Frank was actually innocent.

18 LIP WASN'T FAITHFUL TO MANDY

Lip and Blake Shameless

When Lip started dating Mandy Milkovich, fans had hope that he'd finally found someone who would treat him right and whom he could find actual happiness with. Lip was clearly attracted to Mandy and they had great chemistry, but for some reason, he just couldn't stay faithful to her.

When Lip discovered a grown woman in his neighborhood was once arrested for being with a teenager, he pretended to be significantly younger to prove that she hadn't changed and was a threat to the kids in his area. He succeeded in tricking her, and proceeded to engage in inappropriate activities with her even though he was dating Mandy at the time. When Lip admitted what he'd done to his girlfriend, she was understandably upset and Lip failed to recognize that what he'd done was wrong.

17 LIP WENT BACK TO KAREN WHEN SHE RETURNED

Lip and Karen Shameless

When Karen returned to Chicago, Lip was in a fairly happy relationship with Mandy and seemed to have finally gotten over his manipulative and cold-hearted ex. He and Karen left on very poor terms after Lip realized that she never truly loved him and was an overall miserable and negative human being, yet he still couldn't stop himself from returning to her when she came back to town.

Mandy was a far better option for Lip because she actually cared about his future and wanted him to go to college and reach his potential, but Lip's attraction to Karen kept him from thinking logically. Karen and Mandy's heated rivalry led to Mandy hitting Lip's ex with her car, and Lip found himself unable to be with either of them.

16 HE DIDN'T EVEN LIKE AMANDA

Lip Gallagher and Amanda Shameless

When Lip first met Amanda, she was his roommate's friend with benefits. He and Amanda didn't get along because she disapproved of his smoking and he wasn't thrilled about the noises she and Ron would make in their bed at all hours of the night, but when Amanda randomly crawled into his bed, he didn't stop her and the two unlikely lovers started to engage in an extremely unconventional relationship.

They started out as just casual partners, but after Amanda made Lip meet her parents and go to a sorority event with her, she started developing feelings for him. Lip didn't reciprocate those feelings, but he didn't call off their relationship either.

15 LIP TREATED amanda POORLY

Lip Amanda Shameless

Lip never cared for Amanda the way he cared about most of the other women he dated, but she may have been more of a positive influence on his life than any of his other girlfriends over the past nine seasons of Shameless. Lip had trouble managing his time and responsibilities while in college, but Amanda was happy to create schedules for him which helped him be a more productive and effective student. Amanda's scheme to trick her parents into paying Lip to break up with her also earned Lip several thousand dollars, and her father ended up liking Lip enough to offer him an internship, so he may have been able to have a bright future with her.

Lip realized that his life was getting better while he was with Amanda, but that didn't stop him from sabotaging their relationship by pursuing women who he was actually attracted to. His inability to recognize how much he was hurting Amanda ended up being his undoing.

14 HE PUT HIS COLLEGE CAREER AT RISK

Lip Gallagher and Helene Shameless

When Lip started a new semester at college and discovered that his schedule was blank, he was shocked to discover that his family never gave him the documents needed to renew his financial aid. He was forced to beg his critical theory professor Helené Runyon to take him on as a student, and when his pleas weren't enough to convince her, he used his flirtation skills to change her mind.

Lip successfully wooed his professor, but if she wasn't the type of woman to accept his advances, he could have been expelled for acting so inappropriately around a professor. Lip was also smart enough to know what sort of consequences can come from dating a professor, but that didn't stop him from continuing to pursue Helené.

13 LIP DIDN'T CARE THAT HELENE WAS MARRIED

Lip and Helene Shameless

For some reason, Lip has always been attracted to emotionally unavailable women. He dated Karen knowing that she was promiscuous and likely couldn't be trusted to remain faithful to him, he was with Amanda even though they started out as enemies, and when Helené revealed that she was married, that revelation didn't deter Lip from continuing their relationship.

Helené's husband knew that his wife liked being with other men and actually supported her relationship with Lip, but their marriage should have made Lip realize that he shouldn't expect a future with his professor. It didn't. Lip was blinded by his feelings for Helené, and allowed his heart to get crushed when their relationship inevitably came to an end.

12 HE NEVER SUSPECTED THAT AMANDA MIGHT GET JEALOUS

Lip's relationship with Amanda was always supposed to be completely casual and void of any real emotions, but it was clear that things had changed for Amanda and that she was actually in love with Lip. He remained oblivious to this development, though, and thought it'd be okay to talk about his relationship with Helené in front of the co-ed who he still thought was just his friend with benefits.

After a while, Amanda couldn't contain her jealousy and was furious about how much Lip had been neglecting her. She posted images of Helené found on Lip's phone online, in order to sabotage the couple and try to get Lip back all to herself. Shameless fans totally saw this coming, and Lip should have too.

11 HE LET HIS feelings for HELENE wreck HIS FUTURE

Lip Gallagher Shameless

If Lip had just stayed with Amanda, he probably would have graduated from college and been on the fast track to starting a great future for himself. Unfortunately, his relationship with a professor ruined everything. He was kicked out of the dorms and stripped of his position as a Resident Advisor, he lashed out at the school for firing his married "girlfriend," and Helené's refusal to continue their relationship after it was exposed caused Lip to turn to substances for comfort.

Lip is probably the most intelligent character on Shameless and he's continuously expressed his desire to be nothing like his father, but his reaction to the Helené break-up made Lip seem as self-sabotaging and immature as Frank is known to be.

10 HE WAS WITH A LOT OF GIRLS AFTER HIS BREAK-UPS

Lip Shameless

Lip doesn't know how to be single, so when Helené put an end to their relationship, he immediately jumped into bed with countless sorority girls in an attempt to stifle his extreme loneliness and get over the woman who crushed his heart into a million pieces. None of these other girls were able to help him move on, though, and he found himself completely unable to perform.

While Lip is known for being one of the most mature Gallagher children, his reaction to the Helené break-up proved he's not quite the adult he tries to pretend to be and still has a lot more growing up to do.

9 HE FELL FOR A MOTHER

Lip Gallagher Sierra Shameless

Lip's next relationship was with Sierra, one of his diner co-workers who also happened to be a mother. After a few dates, Sierra realized that she was becoming incredibly comfortable with Lip and actually asked him to take things to the next level with her and become Lucas' father, but Lip recognized that he wasn't nearly ready for such a large responsibility.

That should have been the end of Lip's pursuit of Sierra. She was a mother looking for a man who could take care of her and her son, and that didn't fall in line with what Lip was hoping for. Yet, for some reason, he continued flirting with Sierra and leading her on. They both would have been better off fully separating and seeking out partners that better suited their particular needs and desires.

8 HE wrecked HIS RELATIONSHIP WITH SIERRA

Lip Drinking Shameless

Even though Lip and Sierra wanted different things, they continued to see each other and actually seemed to have a fairly healthy and stable relationship. Sierra was a positive influence in Lip's life and was very supportive of him, but when the Chicago Polytechnic Institute's disciplinary committee refused to expunge Lip's record and let him re-enroll in the school, Lip turned to substances instead of Sierra to help him cope with his sadness.

Sierra's ex Charlie, who was the father of her child, had a substance abuse problem so Lip's excessive partying hit a little too close to home for her. When Lip attacked Charlie, it was the last straw and Sierra broke up with him.

7 HE ASKED OUT ONE OF SIERRA'S FRIENDS

Sierra Shameless

When Sierra ended things with Lip, he yet again found himself at Helené's doorstep begging her to take him back. She refused, and Lip became lonelier and more depressed than ever. He normally had no issues finding a new girl, but suddenly Lip lost his mojo and entered into his longest dry spell ever.

Lip continued trying to win back Sierra, but when that didn't work, he asked out a waitress at Patsy's, the same diner Sierra worked at. She was flattered, but turned him down since he was Sierra's ex and she and Sierra were friends. Lip probably should have known not to ask someone close to Sierra on a date, especially if he hoped to someday get back with her.

6 HE DIDN'T EVEN ENJOY BEING WITH EDDIE

Lip Gallagher and Eddie Shameless

Lip's loneliness and constant complaints about women kept him from being productive at the bike shop he was working at, so his co-worker Eddie agreed to enter into a casual relationship with him so his work ethic would finally stop being hindered. She took complete charge in these encounters, something Lip was definitely not used to.

Lip didn't seem to enjoy being with Eddie at all, and he dreaded how bruised and beat up he'd become after being with her. Yet, for some reason, he never called off their bizarre relationship. He truly and tragically believed that being with Eddie was the only way to help him focus on his responsibilities again.

5 HE was WITH EDDIE even though HE LOVED SIERRA

Eddie Shameless

Most of Lip's motivation to sober up came from his desire to work his way back into Sierra's heart. He helped babysit Lucas during Sierra's dates with Charlie and did everything he could think of to prove to her that he really was changing and maturing.

Even after he realized that he was in love with Sierra and wanted to be with her, however, Lip continued his relationship with Eddie. They were intimate with each other almost every time Lip went into the bike garage for work, and when they finished, he went right back to pining for Sierra. That's definitely not normal behavior for a man hoping to prove himself to another woman.

4 HE ENCOURAGED SIERRA TO GIVE HER EX ANOTHER CHANCE

Lip Sierra Charlie Shameless

In an attempt to pull Sierra away from Charlie and back into his own arms, Lip tried to sabotage Charlie by giving him a pizza which was topped with substances. When Charlie showed up to one of Lip's AA meetings, however, he realized that his rival for Sierra's heart was actually a good guy who wanted to change so he could be with his family again.

Later, Lip discovered that Charlie had gotten another woman pregnant and instead of telling Sierra, he actually promised Charlie he'd keep it a secret. Charlie begged Lip to help him convince Sierra to forgive him, and Lip actually went to Sierra's house intending on telling Sierra to be with Charlie instead of him.

3 HE BROKE THINGS OFF WITH SIERRA after THEY CONFESSED THEIR LOVE

Lip and Sierra Shameless

When Lip went to Sierra's house to let her know how much Charlie loved her, Sierra surprised him by kissing him. Lip couldn't help but kiss her back, but he eventually decided to leave because he didn't want to be the reason Sierra left Lucas' father. When Sierra's father got out of jail, Lip staged a fight to land him back behind bars to protect her, and Sierra told Lip that she loved him. Lip was still torn about what to do with Sierra, but he admitted that he loved her as well.

It seemed like Sierra and Lip were finally ready to be with each other, but almost as soon as they confessed their intense feelings for each other, Lip insisted for Sierra to give Charlie yet another chance. He explained that he might not really love her as much as he thought, and Sierra was so hurt that she told him to leave.

2 TAMMI MOCKED HIS SKILLS

Tami Shameless

Fiona Gallagher has jumped from dysfunctional relationship to dysfunctional relationship over the past nine seasons of Shameless, but she hasn't had nearly as many partners as Lip has. Lip is definitely the show's most promiscuous main character, but apparently, despite all of his experience, he's not particularly impressive.

Lip slept with Brad's sister-in-law Tammi after Brad's wedding, but when he tried asking her out on an actual date, she turned him down and mocked his skills. This was definitely a major shock for Lip, because he'd never received such a complaint before.

1 HE FINDS FLAWS IN EVERY SINGLE RELATIONSHIP

Lip Mandy Shameless

Ian Gallagher and Mickey Milkovich were able to find a slightly happy ending with each other in the ninth season of Shameless, but fans probably shouldn't expect Lip to find his soulmate anytime soon. Lip has yet to enter into a relationship where he wasn't able to list several glaring flaws with his partner, and it seems like he's simply incapable of finding happiness with another person.

Most of Lip's girlfriends and flings have had a variety of character flaws, but even when he finds himself in stable relationships, he manages to ruin them and take issue with whoever he's with. He probably could have been happy with Amanda, but he never really gave her a chance, and his life with Sierra and Lucas could have been great but he felt too guilty taking Sierra away from Charlie. The greatest roadblock Lip seems to face when it comes to reaching his full potential and finding love seems to be Lip himself, and unless he starts learning from his mistakes, Lip is going to keep falling into these same patterns for years to come.

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What other things about Lip's relationships on Shameless don't make any sense? Let us know in the comments!

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