Companion upgrades?
 

I am CM Gold and get upgraded 90% of the time when traveling individually.

How does the travel companion upgrade request work? They told me one must separate the tickets if purchased together, but what are the chances like for upgrades?

You do need to split the PNR, you can call in. Some agents will remove the row 5 seat selection, if applicable, from your companion right away, others won't bother

You will get upgraded at ~T-48 as usual, depending on space

Your companion will get upgraded at the gate at ~T-1. I believe your companion is actually ahead of anyone with their own silver status, who now also get gate upgraded (along with everyone on promo fares) - not 100% sure on this

If you do not split the PNR, then you would likely get upgraded at about T-1.5, and your companion would be eligible again at the gate at ~T-1

Could you clarify what the "5 seat selection" means?

BTW, my companion would be my 5 year old son, so obviously if I'm upgraded and he is not, then we're both going back to Economy.

Row 5 is generally regarded as the best in Economy - others prefer the 2nd exit row

Row 5 (6 & 7, and exit rows) are "premium" rows, which are designated for Silver+. Some agents will remove the non-status passenger from one of these rows if you split the PNR, others do not

If you are not going to sit apart on the plane, then you may as well not split the PNR, and just see if you are both lucky at the gate

You know how to see how many business seats are booked/remaining for your flight(s)?