2. Played by Emma Watson
We already know that Emma Watson can pull off short hair — she looked great in Perks of Being a Wallflower. She also has just the right level of sass and condescension necessary to play Carrie’s future BFF.
4. Played by Saoirse Ronan
It’s probably going to take an Irish actress to capture the innate grace of Charlotte, and Saoirse Ronan certainly seems up to the task. Like Charlotte, she also has that nice balance between innocence and sensuality.
5. Samantha Jones
6. Played by Lindsay Lohan
Older than the others and, well, more experienced. Lindsay has done a lot of living for her years, which makes her feel just mature enough to take on Samantha. And she has the voice down already.
7. Mr. Big
8. Played by Joseph Gordon-Levitt
Few actors have the effortless charm of Joseph Gordon-Levitt, who could easily step into Mr. Big’s sizable shoes. He’s a little too old for high school Carrie, but don’t worry, they’ll become more age appropriate with time.
9. Aidan Shaw
10. Played by Michael Angarano
Before Aidan was a clean-cut adult, he was a scruffy hippie, and Michael Angarano can handle that. He’s handsome, but he looks like he could be even more handsome if he really pulled himself together. That’s totally Aidan.
11. Jack Berger
12. Played by Freddie Highmore
The eyebrows alone! But Freddie Highmore also works as Berger because he’s got that goofball charm — he’s kind of a dork, but he’s weirdly cute about it. Try to forget that he’ll eventually break up via Post-It.
13. Aleksandr Petrovsky
14. Played by Hugh Jackman
We’re not going to see The Russian as a teenager — that would mean going back a couple decades further in time. But how about Hugh Jackman as the famous dancer? I can imagine plenty of high school girls crushing on him.
15. Richard Wright
16. Played by Michael C. Hall
Again, he’s no teenager, but he’s still a stud. Michael C. Hall and James Remar play a father and son on Dexter — not blood-related, but the resemblance is there. Plus, Hall can turn on the unctuous charm, essential for a hotel magnate.
17. Smith Jerrod
18. Played by Kodi Smit-McPhee
Remember, Smith would be a kid in the ’80s: Kodi Smit-McPhee is probably a bit too old, but this is TV, so we can fake it. Like most models, I imagine Smith would look a little awkward in his younger years.
19. Trey MacDougal
20. Played by Nicholas Hoult
Ah, Trey. So handsome and so … boring. But he was young once, and likely scary handsome. The dreamy Nicholas Hoult would just have to stiffen it up to play Charlotte’s future ex-husband.
21. Harry Goldenblatt
22. Played by Michael Cera
It’s Harry with hair! OK, use your imagination here. Namely imagine him bald. What’s important about Michael Cera is that he’s got that nebbishy appeal: even when he’s awkward, you could easily fall for him.
23. Steve Brady
24. Played by Anton Yelchin
Anton Yelchin can look dapper, but slap some glasses and a slouch on him, and he’s a total dweeb. Like Steve, he’s sometimes a schlub but always completely lovable. Don’t forget to add some curls to his hair.
25. Stanford Blatch
26. Played by Johnny Simmons
Is Johnny Simmons too handsome to play Stanford? Maybe. But imagine if Simmons let himself go a little bit and lost his hair — stranger things have happened. Besides, Stanny is still cute, in a shy, boyish way.
27. Anthony Marentino
28. Played by Paul Iacono
Out actor Paul Iacono could be great if he hammed it up to play Anthony. He’s got the look, and he could master the sass, especially if Mario Cantone were willing to give him a few lessons.
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