I see the first option as where we're going slow enough to bat one's eyes, exchange sweet nothings, and cuddle. The second is flat out, pedal to the metal, sucking the will to live out of each other - you know, like we usually enjoy doing. Kapeesh?
I suggest leaving from Wonger's Wait (Shelbourne & Hillside) at 6 sharp to get that 15-minute jump, and doing either this (36K; c. 1:27 at 22 km/h avg), or this (37K; c. 1:42 at 22 km/h avg). I think I prefer the latter. (I'd love to get into Francis King on a weekday!)
We can always fiddle around, cut a few corners as needed, and we shouldn't have to rip either route too hard to catch the tail-end of cawfee...
Dark forests are fun! Thanks to all of you for putting up with the somewhat unsocial pace getting out of town. A couple of mechanicals cut back our ambitions a little—but it's amazing how far out you can get before heading in to the office.
Half our group was in a hurry to get home, so we split where Highland/Watkiss comes down and meets the convergence of Highways 1 and 1A. Our little E&N group did a small diversion into Portage Park, but this flyby provides a handy visual of just how much slower the E&N bike path is (with all its car-centric intersections etc.) The Goose group beat us to the Johnson Street bridge by a handy five minutes: