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Well he did take Allie on a romantic weekend away to the lighthouse just so he could say 'I love you' for the first time, so maybe he'd do something even more special for a marriage proposal? Weekend in Paris? A cruise? I can see him getting a bit too carried away with the plans, desperately trying to make it the perfect moment!
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I could see him trying to make it all this big romantic thing and then Allie telling him something like "the proposal IS the romantic moment."