However, their relationship did have its bumps, most notably when it came to Trinket. The bard thought the bear was useless and advocated for him to be left behind multiple times, all of which were met with Vex either becoming angry or outright ignoring him.
When Vex died in the Raven Queen's tomb, Scanlan mostly stood back and watched during the ritual to bring her back. However, as soon as she was revived, he quietly walked up to her and handed her money, obviously upset over her death and glad that she was alive again.
After stealing Gern Blanston's flying broom and being unable to get it to work, Vex turned to Scanlan for help because of his arcane knowledge. Vex jokingly "seduced" him to get his help, and Scanlan invited her up to his room in the mansion where she found servants playing music for them. From there, she revealed she stole the broom and Scanlan expressed disappointment in her actions, something Vex admitted she felt guilty about. Scanlan agreed to help her in return for an unspecified favor in the future. Vex agreed, and he assisted her in finding the magic word to make it fly. He would later call in this favor, getting her a black, pointed hat that she had to wear while flying.
In Ank'Harel, Scanlan was swindled out of an enormous amount of money in his quest for fusaka. This revelation caused him to become incredibly upset. Vex's perception allowed her to notice her friend's agitation and she talked to him about it, and when she found out what happened she promised him that she wouldn't tell anyone.
When Scanlan died for the second time, Vex dropped everything to help. She teleported to Kymal with the help of Eskil Ryndarien in order to send Scanlan's daughter Kaylie to Whitestone. When she found the younger woman was hesitant to go, Vex poured her heart out to Kaylie about her own broken relationship with her father and told her that she should pursue the relationship with her father, since she's lucky enough to have one who's interested in her. Kaylie eventually agreed, and Vex spent the night alone in a city she didn't know, unsure of Scanlan's fate. Midway through the night, Allura contacted her about the ritual's success and Vex ran downstairs in the tavern she was staying in, screamed about how Scanlan was alive, and bought expensive alcohol to celebrate, even getting Trinket a bowl of ale.
Vex's happiness didn't last, however, as when Scanlan awoke from his comatose-like state he became furious that she brought Kaylie, blaming her and the rest of Vox Machina for ruining his chances for a relationship with her. Scanlan then turned on his friends as a whole, at one point even saying that they only went to the Feywild to fix her and Vax's daddy issues. Vex angrily insisted that they all cared about him but he rebuffed them. Eventually, Vex yelled at Scanlan that he should go talk to Kaylie and treat her like a daughter instead of like a sacred object. Scanlan relented and agreed to talk to Kaylie, deciding that he should've been with her in the first place. Scanlan then left the group to travel with Kaylie. Vex angrily cursed the fact that he didn't tell them anything about his life, then turned around and cursed the fact that they didn't ask either.
After Scanlan left, Vex stopped wearing the hat he gave her while she flew, a sign of their broken friendship.