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You know what, I like this story. I like this screenplay. You're writing style is very clean and efficient: it gets the job done. I like the protagonist, Jamie, the neurotic lawyer, even though she over-rationalizes everything and has no sense of humor just like every heroine in every romcom you've seen since 2000. I like the pace, I like the scenarios, even if some of them are a bit cliched. And god, if most of the dialogue, and the jokes here are not SPOT-ON, I don't know what is. There is some truly great stuff here in that respect.
Some of my favorite lines...
Shawn: If the shoe fits, buy it in every color. (Not even sure I know what that means, but it sure worked in context.)
Jamie: You don't look great for your age. My great-grandfather has more sex appeal than you -- and he's dead. (BURRRRNNNN!)
Alarm clock: You’re 35. You’re old. You’re not married. You have no kids. (So great, because I can just hear the voice in my head)
Now to the bad. The results would be tragic if you tried to sell this screenplay right now. Just this year, we've had not one, but two single-woman-tries-to-have-baby-on-her-own movies hit theaters (The Back Up Plan, The Switch), not counting the other movies in the same vein that have been produced in the last five years alone (Mother and Child, Baby Mama, etc.) Keep in mind that most of those movies have underperformed or outright flopped. Honestly, your script, even if it is a little rough around the edges in this draft, is better than all of those movies, but it probably wouldn't be produced because there has been such a flood of movies with a similar concept. Ouch.
Also, the weak, generic ending does not work for me. Jamie and Shawn have spent approximately 6% of the movie together, yet we're supposed to believe they're head over heels in love with each other? Bulls_hit. This is a severely underdeveloped romance, it felt tacked on and rushed, and honestly, Jamie just seems like she's desperate at this point, like she is having the single-mom jitters, and will do anything for companionship.
It needs some reworking, maybe come up with a fresher take in some spots and gut the hell out of the romance (although there really isn't much of it to gut.)
Good job on digging this little diamond out of the dirt. I read it and thoroughly enjoyed it. But I'm gonna have to disagree with your above statement where you said it would be tragic if she tried to sell this script right now. Movies like The Back-up Plan, The Switch. etc, will be long forgogtten in the few years time it takes to produce this into a film. This script couldn't be more ripe for the picking than it is now, IMO.
Screen Dreamer, if you're out there, nice work. This script is snappy, intelligent, funny and heartwarming at times. I think you've got a hit on your hands.