cherrystainedd
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- Parts 107
On the Upper East Side, there are two things money can't guarantee: an acceptance letter and first place.
Anastasia Whitmore has spent her entire life being exceptional. She has the grades, connections, reputation, and carefully planned future to prove it.
There's only one problem. Nicholas Calloway.
St. Jude's golden boy, heir to a name just as recognizable as hers, and Anastasia's biggest competition.
For years, they've competed over everything-grades, rankings, awards, internships, and anything else that might put one ahead of the other. Neither remembers how their rivalry started, and neither is willing to end it.
But when their futures put them in direct competition for the same coveted Ivy League opportunity, their rivalry becomes an all-out war.
And with Gossip Girl watching, late-night study sessions start looking like secret rendezvous, arguments become harder to distinguish from flirting, and the person Anastasia is supposed to hate might be the only person who truly understands her.
They've spent years trying to prove which one of them is better.
Now they might have to figure out what happens when winning means losing each other.
After all, there may be plenty of Ivies-but there's only room for one at the top.
XOXO, Gossip Girl.
OC X OC
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Started- 8-16-2026