Several months after the incident with Frank, Ian is still trying to improve his chances of getting into West Point, while helping with the financial stability of the family. He also now has regular contact with Lloyd, which has turned into somewhat of a friends-with-benefits relationship.
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After Ian is interrupted, the boy pleads with Ian not to tell anyone then Mickey slightly beats the boy up who runs off. Mickey and Ian have sex and then start catching up from an interval of separation. Ian feels confused over whether Mickey actually likes him or not, especially after he has sex with a girl from their neighborhood. Ian asks Mandy for some advice about knowing if a guy is attracted to you. Mandy says that he would know it when he looks in his eyes. The next day Ian saves a kid from Mickey's wrath.
Ian then tries to stare at Mickey's eyes, seeing if there was the supposed "look", but Mickey only asks, "The fuck are you lookin' at? Mickey starts becoming jealous because Ian is seeing the other men. Eventually, Lloyd reveals that he is pansexual when he is kicked out of his house and calls Jimmy soon after. When Lloyd and Jimmy come back to the Gallagher house after drinking at The Alibi Room , the older man seems to want to reach for Ian, but he falls down because of his drunken state.
Jimmy offers him to let him sleep on the couch. He apologizes, then continues walking down the hall. He climbs into Lip's bed with no clothes on, believing he is Ian. Lip reacts loudly, saying that Lloyd has a boner and almost beats him up until Fiona walks in to intervene. Lloyd looks around and then says he was looking for the bathroom because he was going to take a shower, trying to hide the fact that he was looking for Ian. Jimmy takes his dad downstairs, and Fiona asks Lip if he was sure Lloyd had a boner, leading Ian to admit that Lloyd had been looking for him and that the two have been dating.
He adds he did not know Lloyd was Jimmy's father when he met him at the club. Lloyd later asks Ian if he could break into his house to steal back his belongings since his soon-to-be-ex-wife changed the locks. He enlists Mickey and a couple of his cousins to do it.
When Mickey asks Ian why he likes Lloyd, he says it is because he is not afraid to kiss him. Right before Mickey goes into Lloyd's house for the heist, he kisses Ian. Ian waits in the van to be the getaway driver until the robbery goes wrong. She ends up shooting Mickey in the butt. Ian quickly drives away with a bleeding Mickey and his cousins.
He ends up calling Lloyd and asks for his help in getting Mickey mended. When Ian and the rest of the Gallagher children are taken away by child protective services, Mickey lets him stay at his house since his father Terry was away on an extended hunting trip. Terry ends up coming home early and catches Mickey and Ian having sex. He beats both of them, and forces Ian to watch Mickey have sex with a prostitute.
Afterwards, Mickey goes to great lengths to avoid Ian. Eventually Mickey marries the prostitute, since she is pregnant. Ian goes to talk to Mickey, but it goes badly; Ian tries to get Mickey to admit he loves him angering Mickey, who brutally beats Ian. He leaves, claiming to feel better.
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At the end of the episode, Ian cries alone in his room. On the day of Mickey's wedding, Ian helps Mandy set up the chairs. Ian is still so bothered by the fact that Mickey is getting married to a woman that he starts to drink heavily, getting very drunk just before the wedding.
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He tries to confront Mickey again, pleading him not to go through with it. Mickey says it is just a piece of paper, but Ian does not think so. They have sex, and Ian tries to stop him from going through with the ceremony again, but they get interrupted by Mandy, who has been looking for Mickey, who then proceeds with the wedding. Ian continues to drink all through the ceremony and the party. He ends up calling out to Mickey and calling his wife a whore.
During his ranting, he inadvertently reveals to Mandy that he and Mickey have been sleeping together.
Lip tries to take Ian home, but he stumbles and passes out in some bushes. Ian goes to enlist in the army using Lip's identification, because he is not old enough. Ian visits Mandy to ask her to get him something. Mickey tries to talk to Ian, but he tells him that he is enlisting.
Mickey tries to persuade him not to leave, but still fails to express his feelings. Mandy gives Ian what he asked for and he leaves. Mandy asks Mickey if that is all he has to say to Ian, but gets no response. In the season premiere , Ian's family and neighbors do not know of Ian's exact whereabouts, they only know he has "taken off.
Mickey is seen to be missing him and secretly pining for him. In There's The Rub , Lip is approached by military police and finds out Ian used his name and social security number to enlist. The military police show Lip a picture of Ian and ask if he recognizes him; Lip covers for him by saying he has never seen him before. Concerned for his brother, Lip returns home to the Southside and begins looking for clues.
He asks Mickey if he has seen Ian; Mickey says no and asks if Ian is in trouble. With Debbie's help, they find out that Ian has been in touch with Mandy and told her he was staying with an old boyfriend. Upon investigation, they find out it was Lloyd, though Ian stopped staying with him as he had been asked to leave when he damaged Lloyd's property.
Lloyd informs them that Ian is now with Monica. They find and abandoned house full of Ian's stuff, but not him. When they call out for Ian, they are approached by a naked woman who threatens to shoot them. After reasoning with her, the siblings find out that Ian now works at a bar called the White Swallow.
They enter the bar and see Ian serving people drinks. His appearance and behavior are different, he wears a glittery top and makeup, and he acts as though he is on drugs. Upon seeing his siblings, Ian approaches them very enthusiastically and acts as if nothing had happened. He appears manic, offering them drinks and seeming very distracted. He does not answer Lip's questions, but informs him that he has been working at the club for two weeks. He also comments that he finds the idea of the army police searching for him "hilarious", and that he did not "steal anything", he just "started the rotors".
Lip tries to get Ian to talk outside, but to no avail; he is dragged away by security and Ian does not seem to notice. Debbie expresses concern for her brother, asking if there is something wrong with him. Lip tells her that at least they know where he is now, and says he will check on Ian again soon. He eventually finds him who is currently giving an older man a lap dance, who puts an unspecified pill into his mouth. Ian is going by the name Curtis to his clients.