Call me crazy, but I'm putting all my chips on a full sex scene, and yes, that includes penetration.
What he said on the date, about climbing up to her balcony to see her if that's the only option left to him, just has me thinking that this might happen in this episode and it would be such a hugely romantic gesture to Jill that she'll drop her panties faster than you can say "blue-balling".
Even if you went with Sage but are also on the Jill path, I reckon he'd do the same because if she's avoiding him and he doesn't know why, it's the only way he'll get answers, and I feel like, whatever path you took, that there has to be some resolution/progress with the Tybalt blackmail storyline and not have it linger or go unmentioned for 2 or 3 more episodes.