Bolin first crushed on Eska as soon as he saw her at the Southern Water Tribe. Korra claimed that she was creepy but Bolin decided to go make a move on her anyway. Eska hissed when Bolin first approached her but he still flirted with her. Eska thought it would be interesting to spend time with somebody so uncultured so she decided to make him "hers" because he amuses her. She then commanded him to go win her prizes.
Bolin and Eska later joined Unalaq and Korra on a mission to open the southern spirit portal. Bolin brought a snowmobile with a sidecar for two and wanted to sit with Eska but instead ended up driving while Eska sat with Desna. When the group was around a campfire, Bolin was scared of the "ghost stories" and Eska said that she would protect him. Bolin later hugged Korra when she returned safely so Eska froze him and scolded him for making physical contact with another woman.
Bolin was later exhausted because Eska was using him as a servant. He said that he would miss her once she left but Eska decided that Bolin would be going to the north pole with him. Bolin cried and Mako suggested that he break up with her. He tried to multiple times but Eska kept freezing him and threatening to feed him to dolphin piranhas. Bolin eventually tried again and Eska agreed that they were growing apart so she decided that the only way to fix it was by marriage. She placed a betrothal necklace on him and declared that they would marry at sunset. Bolin was frightened but managed to escape with Team Avatar. Eska was enraged and attempted to chase after Bolin. She was later very depressed and blamed Korra for stealing him.
Bolin and Eska later met again during the battle at the South Pole when the former was trying to stop Unalaq from entering the Spirit World. Eska and Desna managed to capture Bolin and Mako and freeze them into blocks of ice. Bolin finally cried over the thought of never being with Eska again. Eska told Bolin that he shouldn't have left her at the altar but Bolin said that he was just scared. Eska kissed Bolin and then freed him. Mako told Bolin that the fake crying was a good job but it turned out that Bolin was not faking.
Bolin later rejoined the fight and decided to fend off the dark spirits who were trying to attack Korra while she was meditating in the Tree of Time. Bolin was nearly dragged off by a dark spirit until Eska came to save him. The two ended up fighting side-by-side and Bolin said that they would face the end of the world together. After the battle, Bolin invited Eska to come live with him in Republic City and even said that Desna could come too. Eska told Bolin that she was going back to the north and that she was just caught up in the moment. Bolin nervously stated that he was as well. Eska said that Bolin would always be important in her organ that pumps blood and that she would remember him fondly.
The Boleska pairing was anticipated before Book Two even aired. In fact, some even shipped it before Eska's name was revealed. The ship especially took off when screenshots were released of the two talking to each other. The speculation turned out to be correct when Bolin and Eska hit it off in the first episode of Book Two. Some began to find the pairing to be creepy when Eska tried to force Bolin into marriage. However, after the finale of Book Two, the love for this ship grew again. Boleska commonly rivals the Borra, Bosami, and Bopal ships.
- Bolin also crushed on Eska's twin brother Desna before realizing that he was a guy.