Originally Posted by
baliktad
Both travellers need to be in a premium cabin for the international segments.
The Partner Desk should have no problems doing this for you. I flew ANC-SEA-LAX and met up with my traveling companion before continuing on LAX-LHR-SIN-SYD, and the partner desk had no issues ensuring we were kept together. It'll have to be ticketed as two separate PNRs, but the agent can put a note in that you're traveling together so as to keep the two of you together should any IRROPS arise. (Of course, whichever flight you select would need to have two award seats available in the class of your choosing...)
Originally Posted by
eponymous_coward
You can take AA to FRA and then hop a quick ICE train to MUC, though. IMO, this is probably a better option than trying to find DL award inventory, as AA usually has lots of FRA availability (though they are shutting down ORD-FRA over winter). This is probably no worse than making you or your partner (or both) go an extra leg on AS to a gateway city, so I'd consider it.
I did the ICE from STR to FRA as part of an LH trip once. At no cost to us, they were able to substitute the train for the plane hop. I tell ya, doing it in conjunction with an LH ticket is the way to go--they check your bags through to your final destination right at the train station and it's a seamless transfer at FRA.

Of course, doing it on an LH itinerary's not exactly an option for you, but it's still an easy transfer. (It would, however, require some out-of-pocket expenditure [reasonable, IMHO], and it's going to be marginally longer than a flight [FRA-MUC is a bit longer than FRA-STR], but it's certainly not a bad option.