The only and one req to get this scene - went with Jill on picnic in EP6. In EP7 you may pick what you want - having a DIK affinity you may try to fight for her, Jill will silently reject MC or having a Neutral or Chick affinity you may decide to not fight for her (to avoid getting on her path with all future consequences).
Bench scene with Jill in EP9 have 5 scenarios:
2 of them are "friendly" and ends well:
a) req to went on picnic with her, but stop any futher advances by not fighting for her or by MC DIK affinity in EP7
b) req to get rare rejection scene in EP8 at her date with Tybalt - you have to pursue only her (no any other MGs or this choice will not be available) but have to fail the last steps (easiest way - have a DIK affinity and choice to fight for her in EP7). Then MC will get a rare Jill / Others choice and selecting Jill will lead to this scene. She will dump MC and he will end up on Others road after that.
2 of them are breakup variations:
a) if you rejected her for J&M or Sage
b) if you rejected her for Bella
The last, exclusive bench scene nor good, nor bad, if you even never romanced Jill, but just decided to choice Bella.
And finally, you're not getting any bench scene if you didn't went on picnic with her or dumped her instantly on first tennis date.
)
