In order for you both to be upgraded, R must be 2 or higher (it is an all or none deal for upgrading multiple people). The major downside is that any single traveler can grab that single R seat.

My suggestion is to cancel the waitlist and split your travel into separate PNR's (assuming your travel companion can be added as a nominee). If your nominee has no status, upgrade them first as you'll be more likely to have your upgrade clear at the gate than a non-status companion (of course seating arrangements may not be desirable by that time).