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I'm going insane trying to get the "middle of the road" ending, lol...
I read the diet book, so I'm trying to eat sugary but make sure I work out, and it's just giving me the letting yourself go route.

I got it once to say something along the lines of "My tummy hurts, but my muscles also hurt from my work out" when I went to sleep one night, which made me think I was on the right track, so I tried repeating it and apparently wound back up on the letting yourself go route again. Feel like I'm going insane!

Game is good though, obviously I'm enjoying it if I'm focused on figuring this out, but for now I'm very stumped.

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You're very, very, very close.  Close enough to have 'accidentally' stumbled on it the day you referenced, where her stomach and muscles both hurt. Spoiler for the difference after the break.











You're hitting two out of three criteria for the Curvy / Fit And Fat / Middle Of The Road route - sugar/carb heavy meals and working out - but missing the third element - sufficient protein. Add some eggs / hamburgers / chicken to your diet and you'll be good to go.

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Edit: With your guidance, I have conquered the challenge! Now to explore other endings... Thanks again, chief!