Answer:
Hm, I think that it would be fun to reverse some of the cliches
Meet cutes is something that gives readers a good impression on a realationship. I think its funny whenever that goes horribly wrong.
Like for example, a cute momment where they're walking home together under the same umbrella but the umbrella flies away, and in a frenzy they run to the closest place they could find to take shelter from the rain. That place could end up being anything from a bar full of motor cyclists, a roller rink, or anything that will drive their realationship fowards in the direction you want to go.
When your having trouble finding plot points think...
- What is the worst thing that can happen to my character?
- What is the best thing to happen to my character?
- What does my character want, why cant they have it?
- What does my character have, why don't they want it?
Haven't read your story yet, but the title gives me an idea of what its about. Maybe your character can find out about the bet, and instead of getting mad, instead they use it to their advantage and manipulate the bet without the other characters knowing. This could lead to a lot of cute and funny momments.
For me, whenever I get writer block I usually listen to different music that I've never heard before or different shows and movies. That sometimes gets me ideas. Other times I just have to wait until it suddenly hits me.