Lucy and Monty

The relationship between Lucy St James and Richard Monty initially starts off rather tense and enemy-like. However, at the story progresses they become solid friends and trust in each other no matter what. Their strong relationship is shown when Lucy helps Monty to understand his feelings for Oliver and develop their relationship, and when Monty later rebels against Helios in order to help Lucy. Although the pair still make rather mean jokes about each other, their insults are just based on a solid friendship of trust and mutual respect.

Season 1
When Monty first meets Lucy after she joins Helios, he is initially very rude and judgemental toward her. Lucy becomes the butt of all of Monty's jokes, and he makes it clear that he thinks she is a bad agent and undeserving of her position with Helios. Their enemy-like relationship begins to soften when Lucy starts returning the same attitude back to Monty, making him realise that she is not an easy target, and when she starts proving herself by completing high-profile missions for Helios. Despite no longer despising each other, throughout the season they still often mock each other, and on one occassion, get into an intense verbal arguement that almost turns phsyical.

Season 2
Two years after Lucy's recruitment into Helios, she and Monty still have a somewhat tense relationship, but it is clear that there is no longer bad blood between them. Their friendship begins to develop when Lucy encounters Monty and Oliver interacting, and deduces that Monty has unrealised feelings for Oliver. Despite Monty initially refusing to accept Lucy's help, he later comes to her for advice. This causes them to become closer and Lucy helps Monty and Oliver to get together, and for Monty to realise his sexual orientation and accept himself. This includes accompanying Monty and Oliver on their first date, along with going with Monty when he confessed that he was gay to his parents.

Later on, Monty helps Lucy to get over her feelings for Messer. Monty has always had a suspicion that Lucy and Messer had feelings for each other, but simply refused to act on it due to rank and protocol. After the Charity Ball, Monty and Lucy are arguing in the garage over which car to use for an upcoming mission when they both overhear Messer and his ex-wife Rachel having an intense conversation. Messer takes his fustrations out on the both of them for eavesdropping, and Monty quickly realises how upset Lucy is over Messer choosing to rekindle his relationship with Rachel. Monty reacts by making cruel jokes about Messer's personality, calling him boring and uptight, which makes Lucy feel better about not being "chosen" by him.

Monty seeks to help Lucy by setting her up with one of his friends, Cameron Fairchild, the armory requisition officer for Helios. Lucy and Cameron, and Oliver and Monty often are seen on double-dates. When Lucy breaks up with Cameron, Monty doesn't seem to mind, but makes her promise to him that she didn't do it because of her feelings for Messer - something which Lucy lies to him about.

Season 3
Throughout the beginning of the season, Monty has suspicions that something is going on between Lucy and Messer, but did not completely believe that they were together due to their issues in the past. He and Oliver are eventually the ones who uncover their secret romance after catching them attempting to have sex in the armory (after going downstairs to complete the deed themselves). Monty becomes angry at Lucy for keeping the relationship a secret, as he realises that she broke up with Cameron in order to be with Messer. He notably does not have the same attitude toward Messer, due to the amount of respect he has for him, and the pair remain friends which irritates Lucy.

As their friendship deteriorates, Monty reverts back to making mean jokes and pulling pranks on Lucy like he did before, which she then reiterates despite Messer asking her not to. They eventually become friends again when they are forced to work closely together on a mission that puts both their lives at stake.

Later, when Lucy and Messer break up and Messer leaves Helios, Monty turns up to comfort Lucy and again insults Messer to try and make her feel better.

Season 4
With Messer no longer in the picture, Lucy and Monty become closer and closer as their friendship develops. When Monty gets married to Oliver, he shyly asks Lucy to be his "best maid of honour". Lucy is surprised at the offer, never knowing that Monty actually considered her as his best-friend, and reacts by making fun of him for his feelings.

When Winter Greene informs Monty and Max that Lucy and Messer have gone rogue together with ExoGen and have orchestrated the attack on Helios, they both react with hostile anger. While Monty initially does not believe the news, he is convinced by Max that Lucy would be willing to give up her soul for Messer. Monty vows alongside Max to capture the two rebels and make them pay for the attack.

Season 5
Following the destruction of Helios Headquarters, Lucy takes a badly injured Messer to Monty and Oliver's house to be treated. Monty arrives home to check on Oliver, and quickly draws his gun and runs into the house when he finds Lucy's stolen car parked across the lawn. He and Lucy have a stand-off, and Monty reveals the lies that Winter has said about Lucy and Messer. In an effort to convince him of her innocence, Lucy lowers her gun, allowing Monty to have a plain shot at her if he chooses to - however, Lucy knows that he won't because of their friendship and the trust between them. After seeming to debate whether to shoot her or not, Monty similarly lowers his gun and agrees to trust Lucy.

As Oliver treats Messer, Lucy and Monty return to Messer's hideout to gather information about ExoGen. After successfully avoiding two agents patrolling through the wreckage, they return to his home and rescue Oliver and Messer from other agents. After killing one of them, Monty has a mini panic attack upon realising that he has completely gone from Helios' side, and he is now a rebel.