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Making intersecting air reservations for two people on two continents

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I will be traveling to Spain this summer and returning to the US with my Spanish friend's 13 year old daughter who will be our guest here for ten days before returning home. I usually plan and reserve my flights on orbitz. Is it possible to do this in a way in which we can simultaneously be booked on the same Spain to US leg of the journey? Do you recommend we use a real live travel agent for something this complex? Any advice would be much appreciated!

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