None of the 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.
20. HE KNEW KAREN WASN'T GF MATERIAL
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
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
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 itted 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
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 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
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 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
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
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 ed 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
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.
