A recently divorced and regimented urban planner takes a job in a conservative rust belt town and falls for a guarded co-worker trapped in a toxic relationship. He learns turning a town around might actually be easier than turning a heart. 

SYNOPSIS:

James Southport needs a change. He's 41, been divorced for just over a year and hit the glass ceiling at work.

He decides to do something radical and take a new job as a town planner in a rural town called Mansfield. Upon arrival James is dismayed to discover the managers and Councillors are very conservative and stuck in their ways and only interested in securing more factories. They look to the past for their future which is at odds with James' ideas and beliefs to move the town forward.

James is angry at himself that despite his meticulous planning skills, he didn't research the place enough and is battling a 'footloose' type town mentality. He considers quitting but his ex-wife Monica encourages him to 'bloom where he is planted.'

James' only highlight is meeting Millie. One of the administration girls who works two days a week in the office. She's a Kate Winslet cross Dana Scully from X-files type. James is immediately drawn to her but she is reserved, cold, short and guarded. She is hiding something but James slowly starts to break the very thick ice.

At a Council meeting, the Council decide to ban bikes at the local library due to kids leaving them lying on the ground. James speaks up and suggests building bike racks might be a better option. This ruffles some feathers but Millie, who is present at the meeting, sees something in James. At the end the meeting, James is in his car when when he sees Millie being picked up by her boyfriend Travis who is verbally abusive to her.

James tries to talk to Millie about this at work but is shut down. Millie says she is fine and not in any danger. James learns through a co-worker that Millie and Travis were high school sweethearts and that Travis was about to join the Army but after a drunken motorcycle accident he was injured and could not join and he has been a heavy drinking idiot ever since. He has not really moved on and spends his time either working at a factory or drinking with his friends.

James and Millie meet by chance at cafe and spend the afternoon walking around town and getting to know each other. James teaches her about town planning and points out things that he would like to change and improve and shares his frustration with the new role. James learns more about Millie as she comes out of her shell but Millie accuses him of deflection and how he avoids having questions asked about himself or sharing about himself. Millie believes the nice guy friendly routine is a way of hiding just as she has her ways of hiding. James, with all his planning nuances, continues to fight to improve the town and also helps a fellow staff member win over a girl.

James and Millie continue to get to know each other with James revealing the reason his marriage failed. James learns from Millie that she went to university to be a teacher and that her and Travis had a life plan of her teaching where ever he was posted. However she was pressured to quit her course and come back for Travis as friends and family said he was spiralling down since he could not join the army. She shares how she has regretted coming back ever since and has lost so many years being stuck with a man who is angry and wont change and takes her for granted. Millie says she still loves Travis, the old Travis she knew and planned a life with.

James and Millie kiss and reveal their feelings for each other though they are confused about what to do. At the work Christmas show, Travis confronts James and warns him to keep away from Millie. At a softball game, James and Travis are both watching Millie play. Travis confronts James which distracts Millie and she is hit fiercely in the head with a softball and knocked out. She is taken to hospital and in a coma.

Travis and James have a physical fight in the hospital carpark. James tells Travis that his problem is he has never had to win Millie over. That he just got her in high school but has never had to step up or self improve or strive or anything that a guy does to win a girl over. James tells Travis that he is wining her over and will win once she is out of hospital and that it's over between Travis and Millie. Millie wakes up and James goes to the hospital to see a clean shaven and nicely dressed Travis at her bedside. He is apologizing and promising to change. James leaves realizing that Travis has actually taken on his inadvertent advice and is going to try and win her over.

A sad and dejected James continues to make improvements at work while Travis and Millie and spend time together and Travis is winning her over. Millie meets James and they fight about the situation. James tries to convince her that the change wont last as he saw it his whole life as a child with toxic men and that he is right for her. Millie says the old Travis is back and she is happy as he was her first and true love.

James attends a welcome back party at work for Millie and has a present for her but Millie announces she is not coming back but leaving to go back to university and finish her teaching degree. Millie sees James and she explains that Travis and her are going to move to the city and Travis has even sold his house to do the move and that he has also found a new lease on life and is looking forward to finding a new job in the city. Millie thanks James, having learned that it was him who has brought this change about and how she can never thank him enough for bringing Travis back to her.

James says he loves Millie and she says she knows but his love is not the right love for her. That his love is still love but it's a clinical facts and figures love and that remembering her favorite things or planning every date to the last detail is not the love she wants or needs but that someone out there will appreciate that kind of love. Millie says James has not only saved the town, but saved her life too. James gives Millie her present. It's a mixed tape of music, just like you did in the past when you liked a girl.

Days later a depressed James goes back to work and is typing his resignation . A staff member comes in with great news about one of James's big ideas coming to fruition. James notices a small flower growing in a pot away from the light in the worst part of room and is reminded an earlier conversation where he was challenged to 'bloom where your planted.' James deletes his resignation letter.

SQUARE LOVE IN A ROUND HOLE