- He visited Alison's memorial in "Please, Do Talk About Me When I'm Gone."
- In "Moments Later" Ian gets engaged to Melissa Hastings.
- In "Know Your Frenemies" Melissa and Ian convinced Spencer to keep the secret of Ian getting Melissa pregnant from Mr.and Mrs. Hastings.
- He offers to help Spencer run away when she becomes a Person of interest in Ali's death.
- Before his death in "For Whom the Bell Tolls" the Liars make a blackmail message for him because they found the videos.
- Previous relationships with Alison and Spencer.
Spencer goes to pick Melissa up from the church, where she has been planning the christening for her unborn child. Melissa can't find her phone and believes she left it in the church. She and Spencer agree to go back for it just when a car comes out of nowhere, colliding with the sisters. Spencer is okay, but Melissa gets injured. It seems that the accident is a hit and run, as they don't know with whom they've collided. While Spencer is busy with the aftermath of the accident, and the baby being monitored, Hanna, Emily and Aria work on trapping Ian. They call Spencer at 7:30, but unknown to them, she is at the hospital.
Back at the meeting point, the girls get a text from "A," warning them to prepare, though the girls aren't sure for what. Emily takes Garrett up on his offer for help and confides in him about the Ian situation. He shows up in his personal car, wearing civilian clothes. Ian fails to show. Instead, a messenger boy with a sack of cash goes in his place, and Officer Garrett corners him. He turns the messenger away without telling the girls what he has done, though the girls have already caught sight of the messenger. Ian seems to have disappeared, leaving his injured pregnant wife to cope with the stress alone.
Spencer goes to the church to get Melissa's phone. She calls out for the Reverend, then begins searching. There, Ian corners Spencer – and it’s not a good situation at all. He calls the anonymous number that was used to text him, and a distinctive ringing is heard from Spencer's bag. She tries to use the fact that Melissa was in an accident to derail him, but he doesn't go for it. So, she takes the flashdrive from her bag and holds it up. He starts chasing her, and she throws her flash drive to throw him off her trail. (It is unclear whether there is a backup copy.) She starts running up the church tower to get away from him, but he is able to corner her. When Spencer gets Hanna, Emily and Aria on the phone, they are able to hear her entire fight with Ian at the church, including his entire plan for staging Spencer's suicide. Knowing how much danger she’s in, they rush to save her and dial 911.
Ian wraps his hands around Spencer's neck and makes a move to throw her down the bell tower. Spencer catches onto the ledge before she falls. Before Ian can ply Spencer's hands free, a figure approaches. Ian seems to know who it is, as he asks, "what are you doing here?" The mysterious figure, (later revealed to be Alison DiLaurentis in A is for Answers donned in "A's" usual black hoodie and gloves) saves Spencer by pushing Ian to what appears to be his death, as he dangles motionlessly, entangled in the church bell's ropes. The ropes envelope his neck and appear as if they have strangled him. Spencer props herself back up to a secure spot and the ledge, just as the rest of the girls arrive to see that she is physically okay, but very shaken.
Later, the girls walk out of the church together, but are stopped when Officer Barry Maple calls them back to ask if their story is a joke. He can see the confusion on their faces, so he motions the girls to follow him into the church. Inside, the see that the bell tower is indeed empty, and Ian’s body is nowhere to be found (He was alive and escaped). Much of the town emerges to see what the commotion is about, and Rosewood is left to wonder just how much truth the girls have been telling.
- His body is found in "Blind Dates" where his death is made to look like a suicide. There was also a apparent posthumous confession note but that was written by A.
- Ian was dead presumably from a bloody gunshot wound to his head
- In Season 3 some of his videos are found and then destroyed.
- In an interview with I. Marlene King, she confirms that Ian did in fact commit suicide, for reasons unknown. Mona was the one who faked the suicide note.