Lisa Stillman

Lisa Stillman is the glamorous owner of Fairfield Stables, a thoroughbred breeding facility that Amy describes as "famous". Lisa was one of the first high-profile members of the Hudson community to champion Amy's unique equine abilities.

Season 1
Nick Harwell passed on Amy's name to Lisa. Amy arrives to look at a horse, Promise, at first she isn't sure if Amy's up to the task due to her young age. She's happy with her attitude so allows her to work with Promise. At the open house Lisa sticks up for Amy when she shows everyone her work with Promise when Val berates her. She later compliments Jack's burgers and the way he is with the girls. He tells him about how she's taken on her nephew since her sister's messy divorce. (Breaking Free)  Lisa buys Ben a new jumping course, that he sets up at Heartland. When she calls to talk to him, he ignores her calls. She tries again and Amy tells her he's at a jumping show. Lou interrupts to tell Amy that Melody's in labor. Amy quickly tells Lisa that Ben thinks she's trying to buy him off with the new jumps so she can leave him there and hangs up. Lisa turns up a few days later to see Ben and runs into Jack, he tells her how generous she was to give him the jumps and invites her for pancakes. She goes to talk to Ben and explains he can come back to Fairfield Stables whenever he wants, he tells her that he would have a few weeks ago but now he's happy there. They hug and she congratulates him on his 3rd place in the show. (Come What May) Jack is reading the article about Gallant Prince, Lisa tells him that he was bred out of Fairfield Stables. When Amy starts working with Prince Lisa stops by to visit him and appologises to Jack for getting Amy involved. While she's there she invites Jack to go to High River to see a horse she wants to buy. Jack insists on driving his truck, which consequently breaks down. Lisa pulls out a picnic and gives Jack turkey and Swiss sandwiches. When she and Dan Hartfield go to check on Prince's improvements she's happy to see how far he's come when Jack knocks Dan down a peg when he starts throwing his weight around. She tells him that he can say whatever he wants to Dan as he's no longer her husband, which cheers Jack up. (Out of the Darkness) Lisa goes to Maggie's to buy some fishing gear for her trip with Jack. They head up to his Fishing Cabin and he teaches her to fish. They start getting closer and end up getting to know each other and talking about Lyndy Bartlett. They drive back to Heartland and are about to kiss when they notice everyone is sat on the porch watching. In Maggie's Lisa talks with Val about how she's not happy Ben is training with Ashley, when Maggie shouts to her that she's happy about her and Jack. Val is shocked by this news. (Thicker Than Water) Lisa arrives at Heartland to spend some time with Jack. She enjoys seeing how proud he is after Amy wins the Fall Finale. (Coming Together)

Season 2
Lisa sits with Jack in Maggie's she tells him she thinks he should let Lou go for it since she just gave up a big opportunity in New York. (Ghost Horse) Lisa joins the group of the cattle drive in Ray Philips' memory. She brings Jack a gift of a new softer saddle with has been recommended for arthritis, Jack isn't too keen. In the evening, she asks jack if he'd like to go to bed early and he finally talks to her about treating him like he's old. She confesses her love for him, knowing he won't say it, telling him that's how she shows her love. They kiss and dance. When they get back to Heartland she admits she was wrong about the saddle and takes it back. (Dancing in the Dark) Lisa joins the group to look over the pictures taken on the trail ride. (Corporate Cowgirls) When Amy tells the others about Mark, Lisa is confident she will change his mind. When Lou hands out the polo tickets Lisa gets excited but is disappointed when Jack is adamant he's not going. When Lisa starts avoiding Jack, they run into each other in town and he tells her to not avoid him just tell him if she no longer wants to be with him. Instead, she shows him a new shirt she bought him but he still tells her that he's not going to the Polo. She and Lou go to the polo match and is surprised when Jack arrives. (Holding Fast) Lisa brings Diva Girl to Heartland for Amy to work with. She tells her that she and Dan bought Diva as a yearling and has had her sold and returned three times because of her mood swings. They also called her Diva Girl the Divorce Horse as she believes she's cursed and has broken up every couple that's owned her including her and Dan. Amy tires riding her and tells Lisa she doesn't see nay problem, Lisa tells her she's on her best behavior but each day her mood will change. When Mackenzie arrives, she takes an instant liking to Diva. Lisa requests that Diva stay in the stables because if she's in the field she'll get dirty and can't be sold as a show horse. Jack and Lisa have coffee, Lisa asks him how Lou is as she has a friend of hers that knows a guy that would be perfect for her. Over dinner, Lisa learns who Mackenzie's parents are and tells Lou that her plans for a "small " wedding will not be small as her parents will want a massive wedding. She offers to help organize it but Lou declines. Lisa tells Lou about the guy she wants to set her up with and Lou's not happy. The next day, Lisa learns more of Lou's wedding plans and tries to "help" by making suggestions in front of Mackenzie thus taking over the planning and taking it away from all the things Lou has planned. Lou starts to get annoyed at Lisa's constant interfering, she also tells Lou that she passed on her email address and it has been passed on to another friend who passed it onto the guy. Lou is furious that she gave out her personal information to a stranger. When Mackenzie cancels the wedding, Lou turns her anger towards Lisa blaming her for getting involved and changing the plans causing Mackenzie to cancel the wedding. She carries on yelling at her for giving out her information to strangers and they both get upset and Lisa leaves. The next day, Lisa comes by to see the progress with Diva and see's Amy has her in the paddock. She explains to Lisa that she doesn't like being cooped up hence the behaviour. Lisa realizes that she can't be a show horse so decides to gift the horse to Mackenzie. Making a deal that if she breeds her Lisa has her first born. (Divorce Horse)  Lisa goes to Heartland to see Jack and the atmosphere is tense between her and Lou. Lisa goes to Maggie's and vents to Maggie about her situation with Lou and making it tough with Jack. When Lou is practising her speech for the meeting, Lisa comes by to drop off her chilli. Lou rebuffs her and the two end up arguing again and Lisa storms off. Lisa goes to pick up her chilli pot and finally apologises to Lou, Lou explains that it wasn't just her interfering, but her giving her details to a complete stranger made her look desperate. They both make up and Lou tells her that she has a meeting with the guy now and Lisa offers to drive her. Not before giving Jack a smug look. (Seismic Shifts)

Season 3
Jack picks up Lisa when she returns from France, she delights in telling him all about her time away. When they arrive at Big River Lisa tries to keep Jack level-headed and reminds him that he can't be angry about how Tim spends the money he lent him. When he immediately becomes angry Lisa removes herself. After, Jack asks Lisa not to say anything and she realizes the girls don't know about jack lending Tim money. After dinner, Lou tells Lisa how lucky she and Jack are that they make a long distance relationship work, while she's missing Peter, giving Lisa food for thought. When she's leaving, Lisa asks Jack if he misses her when she's away, he admits he does but finds things to keep him busy. The next day, Lisa admits that she misses Jack when she's away and is intent on dragging him with her then next time she goes. Jack is adamant he's not and tells her there's no where nicer than Heartland. (Miracle) Jack and Lisa prepare to go to her friend's wedding, she tries to get them to go in her car but Jack insists he's cleaned his specially. When they break down Lisa tires to call for help but has no service, when she sees the time, and realizes they've missed it. She blames the car for knowing he didn't want to go and breaking down. They're towed back to Heartland and Lisa sees Amy's dress for the formal. After Jack breaks down again, Lisa, Lou, Amy and Ty try to convince him to get a new car, he eventually agrees to look. Lisa goes with Jack to check out trucks, when he starts to be very picky she tries to convince him to have an open mind. When Jack finally gets a new truck, Lisa suggests the go on a trip to test it out, she notices he doesn't seem keen and he finally admits he hates the truck and felt pressure from everyone to get it. He storms out to go to the Fishing Cabin alone. When Amy and Lisa are both feeling ditched they meet up and complain about their men arriving at the same conclusion - men are stubborn. Lisa tries to convince Amy to still go to the dance and has a present for her to help change her mind. Lisa gives her a dress she bought in Paris, when she saw it she thought of Amy so bought it for her birthday but thought she might like to wear it to the formal. The next day, Lisa goes out to the fishing cabin and Jack's happy to see her and they make up. (Man's Best Friend) Lisa  tells Amy about the issues with Lightning Dexter and him  refusing at the gate, she asks for her help but Amy tells her that she's too  busy. Lisa's gutted but decides to sell him as a pleasure horse. Jack sees Lisa and is shocked that she sold Tim a racehorse. She tells him that he's no longer a racehorse, Jack slips up and tells her that Amy's working with Tim to help fix Dexter. Annoyed she tells him that she asked Amy first and she said no. Amy's at the track with Tim and  Dexter, Lisa and Liam (her jockey) are watching when he spooks after  Amy's phone vibrates. Lisa starts to walk away looking upset and Amy follows. She catches up to her and apologizes, Lisa tells her that she expects this from Tim but thought they could be honest with each other. That evening Liam catches Amy and Ty in the Fairfield  trailer, Lisa arrives and demands to know what's going on. Amy tries to explain her theory about Liam buzzing Dexter at the start gate, due to a lack  of evidence Lisa doesn't believe her. The next day, Jack goes to see Lisa and tells her that he talked to Amy and believes her and knows things happen  around racetracks when people think no one's watching. Jack and Lisa confront Liam, showing him the buzzers she found at his locker she fires him. They run into Amy at the tracks and they both apologize to each other, Lisa tells her  she's fired Liam after finding buzzers and they hug. (The Starting Gate)  Lisa finds Tim at the track timing a practice run with Lightning Dexter and her horse, Alberta Comet. She tries to psych him out ahead of the race but Tim gets cocky when he tells her Dexter was faster than her horse. Lisa later complains to Jack about Tim and starts to get worried. Jack tells her not to because it's Tim, he's bound to mess up. She and Jack watch the race and are pleased when Alberta Comet comes in first and Dexter loses. (The Fix)

Family
Ben Stillman

Lisa wasn't too happy that Ben came to live with her, she never felt like she had the same knack that Jack has with his granddaughters. She tries but often her affection comes across wrong. Such as, when she buys Ben a new jumping course he believes this is because she wants him to stay at Heartland. Once she talks to him they soon make up and she tells him he can come back to hers whenever he wants.

Romantic
Jack

Lisa and Jack are friendly together, whenever they are together there is always a little more to it than friendship. Lisa invites Jack to check out a horse she wants to buy, this leads to their first date when they break down on the way there and have a picnic of turkey and Swiss. Jack takes Lisa up to his fishing cabin, the first person since Lyndy died. They have a great time and Jack teaches Lisa to fish. They become a lot closer and have a better understanding of each other.

At the cattle drive for Ray Philips, Lisa pesters Jack by giving him a new saddle for arthritis and making suggestions like going to bed early. He finally talks to her about it and she declares her love for him, knowing he won't say it back. Instead they kiss and begin dancing.

Jack and Lisa admit that they miss each other when she goes to France. She's intent on taking him but h put his foot down and tells her he doesn't think there's anywhere nicer than Heartland.

Career
Horse Breeder

Lisa is the owner of Fairfield Stables where she is a "famous" horse breeder.