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I am looking to do a long two zone trip on my AGR points in a roommette but I want a friend to join me for a portion of that trip. For example both of us travel from NYP to TOL, he gets off and I continue to ABQ. Since the roommette redemption is for two people, is that doable? Anyone try it before.
 
No problem. The redemption rate is the same for 1 or 2 people in a roomette. Just book the reward and tell the agent the name and portion that the second person is joining you, and you'll be all set.
 
Would it be possible to have one friend travel on part of one segment and a different friend travel on a different part of the same segment? on a part of a different segment?
 
Yes and no. If they look at the name on the reservation, John and Bob could pass for each other. However, that may not accept Andrea to pass for John - she could be challenged. Technically you can't, but 99% of the time it's no problem.
 
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Maybe I wasn't clear, or maybe I misunderstood. My starting point is the assertion that an AGR member can make a points reservation for a room (bedroom or roomette) and there is no increase in the number of points required to have a second occupant of the room. (Since I've done it, I'm confident in this assertion.) Also, I am asking about making legitimate reservations, not gaming the system or having a passenger fake an identity.

Could the second occupant change? For example, if I book a roomette from Chicago to Emeryville on the Empire Builder and Coast Starlight, could I have one person accompany me from Chicago to Portland and a different person accompany me from Portland to Emeryville? I would expect each second occupant would need an open sleeper ticket, since the AGR redemption would be Chicago-Portland-Emeryville and neither second occupant would use that itinerary. Thoughts?

A further nuance would have one or both second passengers start or end travel away from the segment end points. Would this be a problem?
 
The same second passenger name must be on the award from the start of the award to the end of the award. The only possible exception is to book to/from a border city. This may or may not work.

If a roomette award is used, a 3 zone award costs the same as a 1 zone award plus a 2 zone award. (35,000 vs 15,000 + 20,000) So if "John" wants to travel fron NYP to CHI or GBB and "Andrea" wants to go ABQ to LAX, you could book a 2 zone award with John and a 1 zone award with Andrea for the same 35,000 points. However if Andrea wants to go from KCY to LAX, both would need 2 zone awards and the total cost would be 40,000 points.
 
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