Laurel and Oliver have known each other since they were young, and they know each other's families very well. The two start dating and are together two years before Queen's Gambit sinks. In that time, Oliver is a playboy, irresponsible guy who cheats on Laurel and she's well aware of how he acts, though not his infidelity. Laurel knows Oliver and recognises how insecure he really is and correspondingly, Oliver knows that Laurel can see him and that feeds his low self-esteem. Oliver regards Laurel as the perfect girl: great in school, socially and academically and a person who will undoubtedly go on to do something great for the world.
He doesn't consider himself good enough for Laurel and so when Laurel, who loves her boyfriend both because and in spite of who he is, wants to commit to Oliver and get engaged, Oliver agrees although he's terrified that he'll lose her when he doesn't live up to the idea he thinks she has of their life together. And so, instead of facing his fears and talk to Laurel, Oliver decides to destroy their relationship by beginning an affair with her smitten younger sister, Sara, who always feels overshadowed by Laurel. Horrifically, Laurel finds out about the affair after learning of Oliver's death when Moira Queen comes by to tell them that Sara was on the boat and is tragically suspected dead as well.
During his time on the island, Oliver talks and thinks about Laurel a lot, suffering over how much he hurt her and upon his return to Starling City expects Laurel to thoroughly hate him forever. Upon seeing Oliver again, Laurel is cold and spares not time telling Oliver she blames him for Sara's death. She is surprised to find herself feeling guilty over her fling with Tommy, who pursues a true relationship with Laurel. Immediately upon his return, during his activities as The Hood, Oliver learns that Tommy and Laurel are together. A drunk and miserable Thea later blasts the truth at Oliver's homecoming party, but Laurel lets him know she needs neither his forgiveness nor permission given what he did to her.
Laurel becomes intrigued with the mysterious vigilante called The Hood and considers his actions heroic. At a party Oliver throws as yet another cover while being investigated for being The Hood, Laurel accidentally walks in on him dressing and sees his scars. Her anger fades momentarily as she finds sympathy for whatever atrocity Oliver has experienced and they share a passionate kiss. Laurel is shocked by her impulse and leaves. After some time Laurel gives into Tommy and they start a relationship and fall in love. Oliver, while feeling he has no right to ever expect a romance with Laurel again, behaves respectfully to both of them and continues his friendship with Tommy, although he secretly is devastated that his best friend is dating the love of his life.
Although Laurel and Tommy are happy, at the beginning of their relationship Laurel has moments where she's aware of her feelings for Oliver. These surface when Oliver dates Helena and the four of them wind up on an awkward double date, and later when he's with McKenna. After Tommy learns that Oliver is the Hood, he's appalled and skirts Oliver for a while, eventually concluding that if Laurel knew, she would choose Oliver over him. This leads Tommy to impulsively end his relationship with a puzzled Laurel. Oliver tries to convince Tommy to reconcile with Laurel and he does, but not before Oliver goes to see Laurel and they end up in bed together. Laurel regrets what happened because she wants to make amends with Tommy and Oliver's hurt. Laurel sees Tommy for the last time when he dies saving her life in The Glades.
After Tommy's death, Laurel clarifies to Oliver that their night together, for her, felt like cheating on Tommy. Laurel is devastated at the loss and begins drinking. Meanwhile, Sara shockingly returns from the dead and their shared trauma and torment quickly catapults her and Oliver into a passionate relationship. Laurel has to deal with multiple burried feelings when Sara returns from the dead, which are exacerbated by Sara and Oliver reigniting their relationship. Laurel is angry with Sara for her betrayal, and what she feels is history playing out before her eyes as Sara continues to be with Oliver.
Oliver gets mad at Laurel saying he's done everything he can to care for her, but nothing's ever enough. Laurel later realises that her anguish mostly stems from how Sara and Oliver's alleged deaths has affected her life for the past five years. She makes up with Sara and tolerates Sara's romance with her ex-boyfriend, while still mourning Tommy's death and taking steps to slowly rebuild her life. Laurel doesn't learn about The Arrow's true identity until Slade Wilson shows up in her apartment to offer up the information.
Laurel supports Oliver and Team Arrow in their quest as superheroes, while still fighting crime in court. After Sara is brutally assassinated, Laurel deals by taking up boxing at the advice of Wild Cat. She starts aiming to become the Black Canary, but is thwarted multiple times by Oliver, who doesn't think she should risk her life when she's not trained enough.
On her deathbed towards the end of Season Four, she tells Oliver that he was the Love of her Life. In the season 4 finale Oliver, despite taking a vow not to kill criminals again after Tommy's death, breaks this vow to avenge Laurel by killing her killer Damien Darhk.
In Season Five it is several times hinted, that Oliver still has romantic feelings for Laurel. Throughout the season he has become more ruthless again believing if he had stayed that way, Laurel would be alive as he still blames himself for her death.
In the Midseason Finale, after returning to the Arrowcave, Oliver encounters a seemingly alive Laurel. It is later revealed in the Midseason Premier, that this Laurel is in fact her villainous Earth-2 Doppelganger, called Black Siren, introduced in the second Season Episode of The Flash "Invincible". Earth-2 Laurel also confesses to Oliver in the same episode that she was in love with his Earth-2 counterpart until he died on the Queen's Gambit in contrast to Oliver. Oliver believes partially out of guilt for Laurel's death that Earth-2 Laurel can find redemption, hinting that he's become affectionate towards Earth-2 Laurel somewhat. Earth-2 Laurel herself, despite being a ruthless murderer, also implies that she is genuinely affectionate towards him too, hesitating when he begged her not to kill Felicity and appearing very conflicted while doing so. Despite Earth-2 Laurel being captured and taken to A.R.G.U.S. Oliver still believes there is hope for her.
After Oliver's abducted by the Dominators and put in a Dreamworld, he finds himself in a "perfect" world were he never went lost at sea, is still with a very much alive Laurel and about to marry her. After realizing that the world is false Oliver leaves, but confesses to "Laurel" that he still loves her and believes she deserved better than him.
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