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Well, I didn't have access to Easy Mode the first time, when I asked Jake out, and was apparently not shy enough for him, I guess, since he ended up dumping me at the end. I did turn it on afterwards, when I was mostly aiming for Adam, but didn't have any luck on either my second or third playthroughs. 

Playthrough 4 finally went better, where Jake asked me out, instead, and I finally got my first happy ending. (For the record, Jake is my precious little cinnamon bun, and I absolutely adore him - especially the story behind how he chose his name.) I was actually heartbroken when he asked me out again in playthrough 5, since I was trying to romance someone else (Dan, at that point - who I also managed a happy ending with). 

So, I've had better luck with easy mode, except for Adam, which is apparently intended. Still, I'm going to try for him again...assuming I can stop myself from dating my sweetheart Jake this time.

Sorry for my earlier irritation. Clearly, this IS a good game, since I've been playing it non-stop for the past I-don't-know-how-many hours. I just wanted someone to love me back, dammit! T_T