broke: doorkeay/gerrymichael (never even met, shipped together purely on the basis of visual aesthetics, no connection on a thematic level other than a gertrude betrayal)
woke: gerryMIKE (enemies to
lovershatefucking; guy whose occupation is hunting down and destroying occult books vs guy who literally sold his soul to one; probably share a taste in music; both highly knowledgeable on forbidden subjects; man who made a faustian pact with one demon to get a different breed of demon off his back vs man who juggles at least a few patronages at once to maintain some semblance of freedom; a ruthless pragmatic and a burnout cynic; in another universe probably would have sat next to one another in the same lecture hall in uni)