Lucy is a stiff-mannered ragdoll. She's constrained by good manners to not put people down, but she can't own up to her own feelings even when they hit her in the face. She fails repeatedly to draw firm lines with men, despite (as another reviewer noted) their obnoxious bad behavior (and in one case returns the favor to another date). Being an uplifting comedy, the movie ends with Lucy finally finding "Mr. Right", who accepts her as-is, and who she can accept for who he is.
The charm of Lucy's character rests in her willingness to see the best in other people. Although one date seems brash and self-absorbed, she sticks it out far enough with him to establish a friendship. On the other hand, this trait leads to her entanglement with exactly the wrong sort of man, despite his blatant disregard for her on multiple occasions.
Lucy is a complex woman, and her dates are complex men. For a short film, this story managed to convey a depth of character rarely seen in the genre. I recommend it to the introspective and people-watchers, but not to folks looking for a pat-story.