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The same reasons that she stayed female at Grace's birthday party. That and as soon as Elliot is "disproved" suspicion could immediately fall on Ellen who has a similar name, looks similar, lives at the same house, and is the right gender. They need to do it in such a way that Elllen is not suspected either.

I think it helps that though they liked and even love each other they were never really in love. Big difference. Nanase dated Elliot as he was as close to the ideal man as she could find among her friends and acquaintances. Elliot on the other hand dated her because he liked her as a friend and when she approached him he really didn't understand the feelings of love and being in love. When they broke up neither of them felt that there was a big gaping hole where the other used to be, and so there were no hard feelings. Sarah and Elliot dating was similar. They've known each other since they were toddlers, and though there were friendship and love, and some lust due to hormones, they were never truly in love. The breakup again showed that neither of them suffered the trauma of having their heart broken, nor were there much anger involved. There were some frustration but not much anger. In both cases some feelings were a bit bruised, but no hearts were broken... The fact that none of them is a selfish a-hole does help.

How does a couple break up amicably? By having the breakup triggered by something other than anger at one another.

And Grace is too perfect for Tedd if you want to go that route. She shows up on Tedd's doorstep out of the blue, isn't phased by Tedd's snarkiness. Knows Tedd better than he knows himself, is interested in the same stuff he is, and encourages his scientific research. The only thing that makes her not some evil spy is the fact that Edward knows her history. Nanase and Ellen, while they've had that one fight over hair. They've been pretty much inseparable, you could say they're perfect for each other as well. Why is it when Elliot finds someone he clicks with it must be someone who's intent is to use him?

Ashley comes off as relatively normal, if surprisingly open minded. if anybody's impossible it's Elliot. the only reason he's not a mary sue is he has internally consistent limits, and his 'too perfect' personality and history are balanced out by his becoming a walking doormat around certain types of people. case in point most people will never have even one amicable breakup, he's had two, and is still close with both his exes. how do you even DO that?!