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Help with booking flights for two people

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I was hoping someone would be able to give me some advice on booking flights in a specific situation. My best friend and I are planning a trip to France, Italy and Austria next summer. We want to pay individually for our own flights, but would like to fly over together (we're flying out of Toronto, Ontario). Also, she will be leaving earlier than me, and I will be staying on for a few more weeks with family in Austria.

So, my question is, what is the best way to go about booking our flights? How do we arrange it so that we are sitting together on the flight over, if we are paying separately? Can we book our flights online? Do we need to go through a travel agency to arrange the details? We'd like to save some money too, if possible!

I've never booked my own flight before, so I hope these aren't stupid questions...thanks for any advice!

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