[X] Tell Rei to meet up with this person and recruit Horaki to be a chaperone in case Rei needs backup if things get out of hand. She's both someone who knows Rei pretty well and is a fellow girl, best of both worlds. Though yes Asuka, you can skulk in the shadows too. Maybe you'll see what everyone else in this country does doing things this way.
-[X] Tell Rei some our own experiences in this subject, the times it went good and bad, and advice on what to do for both outcomes.
You tell Rei that it would be best if she heard this person out. Asuka groans. You think it'd be a good learning experience for Rei, even if she decides to turn this person down (you really hope she does). You tell Rei about some of the love letters you received in high school and how they went (mostly not super well, honestly…you weren't really interested in the opposite sex until you reached university). You teach Rei how to turn someone down politely and what to do if things get out of hand. Rei listens diligently, though she keeps asking "why" when you describe ways a rejection could go bad. She seems rather naïve about the concept of "stalking" in particular. Asuka gets fed up with it and snaps at her to pay attention to what you're saying. Is this deference…? From Asuka…?
You are worried that this confession may not be genuine, given Rei's history of being bullied by her classmates. You're also worried that in the event that this confession is real, that the writer's intentions may be less than pure. As much as you want to see what happens, you don't want to let Rei do all this by herself. You don't think she's quite ready yet. You suggest she get Horaki to accompany her when she meets up with this person. You also tell Asuka she's welcome to accompany Rei, provided she behaves herself, though you think it'd be best if she stayed out of sight.
Pssht, yeah, like she's interested, she says unconvincingly. Rei looks at Asuka blankly, though you get the sense that Rei is examining her more closely than she has in the past. Rei says that's fine, the pilot of Unit-02 can come. Asuka says good, because she'd go if Rei wanted her to or not. If she wanted to, that is, which she doesn't. Asuka goes back to her magazine. You roll your eyes and hope to yourself this isn't a total disaster.
Roll 1d20 to find out how this goes.