I think the only AIF game I ever failed* at was BBBen's Pervert Action: Crisis. From the beginning I tried to have a diverse set of skills and interact with multiple girls. At the end, I ended up in a relationship with none of them.
A somewhat similar type of failure though happened in Goblinboy's games where I didn't get the ending/relationship I was shooting for. I think in my first play of School Dreams 3 I managed to piss both Becky and Molly off.
Now, for me, those setbacks just made me want to start again from the beginning. What are other people's thoughts on the issue? Does the potential for failure, and challenge** to get better outcomes, make the ultimate result more worthwhile, or just frustrating?
*I'm using a broad definition of fail here, I enjoyed my first play, so on that criteria I didn't fail, but I didn't get what I wanted (which was possible to get)
**I'm speaking generally. I think people generally agree that too much or too little challenge isn't desirable, so I'm asking in general is more challenge good?