The quest called "Matchmaker" is potentially obtained in Tien's Landing. If players resolve Quest: The Beaten Baker peacefully, they may obtain this follow-on quest from Ai Ling. Although Ai Ling will have accepted that Baker Bei will marry his fiancée Seamstress Lan, Ai Ling would still like to find a way to lead a more normal life, but does not believe that there is anyone left in Tien's Landing who is unmarried and would be willing to consider her as a possible match. Players have the option of volunteering to look for someone — if they do, this quest begins.
There are three people in town who are plausible options:
- Big Tian, who is found just outside the Boathouse in which Ai Ling is based. If Big Tian is brought to meet Ai Ling, she is unimpressed, saying that he is unintelligent, but the player can say that Big Tian is a good man despite being somewhat slow. However, Ai Ling is not sure she would want to leave Tien's Landing to live on a farm. The Intimidation skill (expressing disbelief that someone like Ai Ling is "afraid to spread her wings") and the Intuition skill (pointing out that leaving town would provide a clean break from Ai Ling's current life) are both able to work, but the Charm skill (saying that Big Tian would be willing to abandon his farm and join Ai Ling's gang) will not, as Big Tian doesn't want anything to do with a gang and leaves. Since he needs no persuasion to visit her, this option yields the least XP, at 1000 upon quest completion.
- Yaoru, who is found on the upper level of the Teahouse. If Yaoru is brought to meet Ai Ling, she criticises his manner of speech, suggesting that he is trying to set himself above her by making himself sound intelligent. Yaoru takes offense at this, but the player can calm him by passing a Charm or Intuition check, convincing him that Ai Ling's spirit is admirable. The other option, an Intimidation check to tell Yaoru that he can't back down now, will not be successful. This route gives the most XP, as bringing him adds 60, and the final marriage check adds 1020, versus 1000 for the other candidates. However, for 60 less XP, players will receive a partner comment when selecting Chumin instead.
- Chumin, who is found in the western part of town. Ai Ling is unimpressed by his initial timidity, but says that she admires his craftsmanship. Chumin says that although he is competent at his work, he is not a good businessman, and admits that he is not financially stable. The player can suggest that Ai Ling could help Chumin on that side of his trade, but even if they choose something else, Ai Ling will make this connection anyway — unlike with the other two potential matches, Ai Ling and Chumin do not actually need persuading by the player to make the match work. Therefore, quest completion will only grant 1000 XP, in addition to the 20 to bring him down.
If the player character is male, he can actually offer to marry Ai Ling himself, but Ai Ling refuses on the grounds that the player character is obviously not looking to settle down and live a quiet life in the immediate future.