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Hi, I purchased this game in January this year. So far I got the ending for Midori, Jenny, Tanya, and Emma. I have no luck with Rachel. How cool do you have to be to get her?

It looks like there are 6 endings but there are 5 girls?? (I didn't count the one with a letter from the character's mom.)

You refer to Summer Session (saying for other users that maybe don't know).
Rachel is very hard, I wasn't able to get her ever myself (I only produced this game but was written by another person). There are some guides in the forums though that could help.
The sixth ending is a "special ending"...

Got all the endings at last...