Ben Stillman

Ben Stillman gets to Heartland when his aunt, Lisa Stillman needs somewhere for him to learn more about other sides to do horse training and their care. While he is at first skeptical, if not straight up rude about Amy's methods, he learns through their use on his own horse Red that they can be practical and useful even to serious show competitors like himself.

Season 1
Ben arrives at Heartland and introduces himself. He's Lisa's nephew and she's paying for him to stay there and learn what they do with horses. He does whatever he can to avoid doing any work and always hands off his horse to be cared for by others. He says he's not into "Pony massage". Ty, Amy and Mallory aren't happy with the way he treats his horse. When he's jumping and refuses he uses a whip to show him who's boss. Amy convinces him to go on a trail ride where she sees that he's afraid of water and Ben again shows his dominance. When practicing jumping Red bucks him and takes off while he's down. When he comes to he helps Amy and Mallory look for him. Amy calls him to tell him she found Red and he heads back to Heartland. When he gets back Mallory tells him about the accident but ben wants to know where his horse is, when Ty brings him back. When Ben thinks about his actions after a chat with Ty he goes to Amy for help to fix his relationship and issues with Red. (Taking Chances)  Ben meets Soraya at the barn and gets roped into helping Lou with jobs for the video. When she tells him and Mallory to move the manure pile they move it under Lou's bedroom window. He goes to Ashley's party with Amy and Soraya. (The Best Laid Plans) Lisa bought Ben a new jumping course and he's helping everyone put it up at Heartland. Once it's up he starts jumping with Red and asks Amy how he did. Lisa calls to talk to Ben but he avoids talking to her. When Amy tells him she can't go to his show he's disappointed that no one will be there for him. He returns from the show and Soraya asks how he got on, he tells her that he came 3rd. Lisa pays a visit and tells ben how proud of his 3rd she is, she clarifies that the jumping course wasn't a bribe to stay at Heartland and he can come back to Fairfield when he wants. He admits that he's starting to like it there. (Come What May) Ben is desperate for Nick to coach him in show jumping, he agrees when Lisa asks him to do it as a favour. When they start training Nick is confused he's not doing better in competition. He asks Amy her opinion and Ben is furious when she tells him he never moves his jumps. When Nick wants to go back to basics to find the problem he storms out of training. He has a go at Amy and starts to blame Red, she takes him out on the jumps herself and proves the horse isn't the problem. Ashley turns up at Heartland and finds Ben in the barn, she is impressed when he tells her he fired Nick. They realise they're alone and they finally get together and "roll around in the hay". It is later revealed that Ben has moved out of Heartland and back to Fairfield. (Born to Run) Ben arrives at Heartland with Ashley and a broken arm after falling off Red. He attends Ashley's after party and goads Amy and Ty about Ashley's jumping and how he's helping coach her. Ty tells him that he's coaching Amy and they'll do better than Ashley. He later helps other friends and neighbour re-build Heartland's barn after the fire. (Rising from Ashes) Ben helps Ashley practice jumping and he convinces her to go to Amy for help with Apollo. At the Fall Finale, he has a go at Ashley when she throws the competition by walking off the course. (Coming Together)

Season 2
In episode 2, Letting Go, Ashley mentions that Ben went away to university.

Family
Lisa Stillman

Ben felt lonely when he had to go to stay with Lisa. He felt like no one wanted him and he was just being palmed off. He starts to feel like Lisa doesn't want him and that she bought him the jumping course as a bribe to keep him at Heartland. They make up and confesses he likes it at Heartland.

Romantic
Soraya

Soraya becomes smitten with Ben from their first meeting, however it's only one way.

Ashley

Ashley and ben often flirt with each other. They eventually get together and Ben moves out of Heartland and back to Fairfield. He trains with Ashley and then helps coach her after he breaks his arm. This appears to finish in between Season 1 and Season 2, it is later mentioned by Ashley that he went away to university.