Siyav has been flirting with Wynn since chapter 3.

Wynn has only just realized all of that was flirting.

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Siyav: This is weird…
Wynn: Just say it already Si!

Siyav: I wanna date!

Wynn: Oh. THAT’S why Shirley had to tell me it was ok.

Siyav: UUUGGHH yes that’s why. We talked it out; she’s been hoping I’d do this for weeks and I figured the shopping trip would work because it was just you and me for once and just…