Grant Stern, the main NPC in Best of Three, is more than a little irritating. His academic pretensions make me grit my teeth and if someone I was dining with ever ordered a cup of tea the way he does, I would probably die of embarrassment. I know men like this. Smart men who have only recently broken out of high school into the world of academia are prone to becoming self-centered and obnoxious. However, because I know men like this, I understand the PC's infatuation with him. It is easy to fall for smart guys, particularly if they are good-looking, and most especially if an underlying current of sweetness can be detected.
The whole of Best of Three involves a conversation between our PC, a young woman struggling with family issues and a growing post-high school malaise, and Grant. The PC, upon seeing Grant again, finds that she has not quite rid herself of the crush she holds for him. It is quite easy to direct the conversation to either end their "romance" or begin it. For the most part, the conversation flows smoothly. Grant comes up with things to talk about even if you fail to think of anything to ask him. There were a few points where the conversation options were rather out of the blue and a few other points where I misinterpreted the tone of the available options. The non sequiturs and unexpected replies to my statements could be mimesis breaking, but were the exception to the otherwise seamless conversation structure.
Best of Three, like all of Emily Short's work, is well programmed and implemented. However, it is not her best work. Some actions that should have been implemented were not. Attempting to say goodbye to Grant at any point yields the message "You terminate your conversation with Grant." Said conversation continues without any sign of having been interrupted. Furthermore, although you are quite plainly sitting in a booth in a cafe, getting up is not implemented. Alas.
Overall, this is quite a charming and interesting game. It can't be called difficult at all, but the prose is quite excellent and the characters have real depth. It isn't Emily Short's best work, but it is certainly worth a playthrough, and then another playthrough to pick up all the conversation options you missed and change the course of the burgeoning (or failing to burgeon) relationship.