Arrow began The CW’s large Arrowverse that has and continues to bring on several DC Comics characters as more shows get added to the network’s line-up. For 8 years, Oliver Queen helped create TV’s Justice League, forming several relationships along the way. However, with Oliver being the broody complicated vigilante that he was, he had some different dynamics with various characters throughout his time. While Oliver certainly got along great with most characters, there were definitely a few people in his life that were messy, to say the least.

With Oliver no longer alive in the Arrowverse, there are a big number of relationships to look at during his life. While not everyone can make it on to the list, these are some of Oliver’s best and worst relationships on Arrow as well as throughout the rest of the Arrowverse.

WORST: Oliver and Laurel (Earth-1)

While they are an item in the comic mythology, Arrow had its own take on the relationship between Green Arrow and Black Canary. In this iteration, Oliver messed up his romance with Laurel Lance on an epic proportion by cheating on his girlfriend with her younger sister Sara. The boat trip that morally shouldn’t have happened ended up changing their lives forever as their heroic journeys began that day.

However, no matter how much Oliver loved Laurel, their dynamic was one of the most complicated ones. From Laurel’s breakdown in season 2 to Oliver’s overall treatment of his best friend, the two heroes had a rough time while Laurel was still alive. Even though they had a good vibe in later seasons, that relationship didn’t go any further after Laurel’s death in season 4.

BEST: Oliver and Thea

With Oliver, his love for his family was always one of his better qualities. While he never had a little sister in the comic books, the creation of Thea Queen was one of the best creative decisions. Seeing Oliver as the protective big brother was always powerful, even if the siblings were at odds from time to time. But when they eventually worked together as Green Arrow and Speedy, it became one of the coolest brother/sister dynamic of all time.

WORST: Oliver and Samantha

Even though Oliver’s son William became a welcomed addition to the Arrowverse, the way his parents met was perhaps not that ideal. Sara wasn’t the only woman that Oliver hooked up while he was together with Laurel. It was revealed later on that he had gotten together with Samantha as their one-night stand ended with her being pregnant.

Even though she was paid off by Moira to lie about her pregnancy, Oliver discovered the truth years later. Their dynamic was problematic, to say the least as he couldn’t tell William he was his father. Oliver also couldn’t tell anyone in his life that he had a son. While things did work out down the line, Samantha died in the season 6 premiere after the destruction of Lian Yu. With her death and their messy background, Oliver’s relationship with Samantha, unfortunately, was problematic as a whole.

BEST: Oliver and Laurel (Earth-2)

While his dynamic with Earth-1’s Laurel wasn’t the best, his relationship with her doppelganger got a slightly better take. Despite Black Siren starting as a villain, there were many instances where he wouldn’t give up on her. Having lost one Laurel, he and his team did what they could to save her. Eventually, Laurel redeemed herself and get on a better path with Oliver, especially in season 8.

WORST: Oliver and Evelyn

It will always remain a mystery why Oliver chose to trust a teenager when he rebooted Team Arrow. Evelyn Sharp started her run on the show as a moody teen who stole Laurel’s Black Canary costume and canary cry right after she had died during season 4. While that situation got taken care of, Evelyn returned in season 5 when Team Arrow was relaunched.

Despite showing potential, Evelyn would turn on the team by joining Prometheus as he was set on destroying Oliver’s life. Her whereabouts are still unknown after she was on Lian Yu when it blew up during the season 5 finale. Regardless if she is alive or not, bringing Evelyn into the team was one of Oliver’s biggest mistakes ever.

BEST: Oliver and Barry

Oliver and Barry Allen’s friendship was one of the best dynamics in the entire franchise since they first met. The duo always brought out the best in each other whenever the actors shared the screen. While Oliver was primarily the mentor in the relationship, they still always taught each other a thing or two about being a hero. With Oliver’s death, this relationship is perhaps the biggest loss to come out of “Crisis on Infinite Earths.”

WORST: Oliver and Helena

What started with potential ended up becoming a disaster as Oliver’s fast-paced relationship with Helena Bertinelli got messy really quickly. As Oliver had just started his crusade as Starling City’s mysterious protector, he crossed paths with Helena who was determined in taking her father down.

This led to Oliver helping her become the Huntress, which initially started well. But it was a premature choice since Oliver was nowhere near in being ready to mentor anyone, let alone someone as emotionally charged as Helena. While their conflict did come to an end in season 2, once she was arrested, their relationship was dealt with the wrong way from the get-go.

BEST: Oliver and Felicity

What was set to be a one-episode gig for Felicity Smoak became a 7-year journey. Starting as the IT-master on the team, Felicity would eventually begin a romance with the leading hero that had its many ups and downs. While they had plenty of disputes, it was abundantly clear that these two were insanely in love. Even though they didn’t have any scenes in most of season 8, the couple would find each other again in the afterlife.

WORST: Oliver and the Monitor

The Monitor, while serving a good purpose, wasn’t the best partner for Oliver when he entered the hero’s life. While helping him save Barry and Kara’s lives during Elseworlds, it meant that Oliver had to take their place as well as sacrificing himself in the Crisis a year later. But the biggest problem with their dynamic is that Mar Novu was always insisting on being cryptic and mysterious while needing Oliver’s help. The least they can do when making someone sacrifice themselves for the sake of the Multiverse is giving some clarity rather than pulling riddles out of a hat.

BEST: Oliver and Diggle

Out of all the strong bonds Oliver made, nothing beats the one he shared with John Diggle from the moment they met each other. Diggle was just as important to Arrow as Oliver was, being the voice of reason and Oliver’s closest ally who would eventually become a superhero himself in their crusade. Their bond was stronger than friendship as Diggle, similarly to Barry, was the closest thing he had to a brother.