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Yes, I believe she was supposed to be 20, and Dawson would have been 17 or 18 as this was his Senior Year in High School. Oh course, seniors in High School usually don't have receding hairlines, but hey, this was Dawson's Creek!
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James definitely looked much older than Greg Smith.
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There was a backstory where we learned that Gretchen dropped out of college after her freshman year because she got pregnant and had a miscarriage, so there were shades of Madison there, although Dawson wasn't the father and she lost the baby.
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Oh my gosh, thanks for the reminder, I remember this now. Yikes.
Dawson’s Creek also did the Mary Kay Letourneau-like story with Tamara and Pacey as well so the show was definitely obsessed with controversial relationships and pregnancies.