The player treats Hailey as she expresses confusion and sadness over Logan's reluctance to confess his romantic feelings to her. Halfway through the level, Logan insists on being treated in the same room as Hailey, attempting to build up the courage to confess his feelings to her. Unlike the day level, where the player had Paige's cooperation to treat the two patients, Ian does not cooperate with the player to treat both patients at once. Since his game "finally found a match," he leaves the player to treat both patients at once by themself. After the level, Hailey tries to get Logan to confess his feelings, but he is once again too nervous to properly do so, and leaves abruptly, leaving Hailey confused and sadder. The post-clear text for Hailey has her saying "Everything will be okay. I think he's just shy," signifying that Hailey is feeling better despite the lack of resolution.
Gameplay
2-player mode
Player 1 treats Hailey while player 2 treats Logan, both of whose patterns are identical to their singleplayer patterns. Unlike Intimate, Hailey is always treated by player 1 before Logan appears.
Transcript
[Level start]
Doctor!
You've gotta help me!
Everything with Logan has been so back-and-forth.
Does he really think that we're just friends?
[Interlude]
A-another patient is insisting on being treated in here as well.
Ah, my game finally found a match.
Gotta run. I have faith in you!
Logan?
Hailey! I want to tell you something!
(No more chickening out...just say it!)
Feeling any better, Logan?
I think so, yeah.
So, what was it you wanted to tell me?
You keep saying that there's something super important on your mind
and then your chest starts hurting. So, what is it?
Oh! Umm, yeah, totally...
It's just that, y'know...we've been hanging out a lot, and...
I always feel like we've been super close, and...
Umm...uh, I'll catch you later! We'll talk about it another time!
(Smooth.)
Oh, okay. Bye, then?
Are those teens officially dating, or what?
I always see 'em walking around, holdin' hands, being all mushy.
Next thing I know, they're crying and everything's all awkward between them.
Teenagers are so DRAMATIC.
Love ain't so complicated! Just ask each other out to a movie and get it over with!
History
Trivia
In-game, this level lists Hailey as being the sole patient. This is untrue, as Logan is another patient the player has to treat in the level. This is likely done on purpose; the Day Shift counterpart has the player only treating a single patient, which sets up the surprise for the Night Shift level to have the player treating both Hailey and Logan at once.
Ian's dialogue mentions his game having "found a match," leaving the player to take care of both Hailey and Logan. This contrasts 1-2, where Paige cooperates with the player and takes care of the second patient. However, in Two Player mode, 1-2 has altered dialogue where Paige simply instructs Player 2 to take care of Hailey. Since 1-2N has no altered dialogue for if Two Player is enabled, this unintentionally makes Ian's dialogue out of place; Paige has demonstrated that it is valid to instruct the second player to take care of a patient, so Ian has no need to bring up the fact that he needs to attend his game, and he should instead instruct Player 2 to take care of Logan.