Author's note: Recently rewatched Caroline in the City and wondering why there's no femslash based on this TV show. So here is some.
Caroline had been living across the hall from an honest-to-god Broadway Cat for two years before she noticed how attractive Annie was. Every morning she nips in to Caroline's apartment to steal coffee and discuss the men she'd just acquired or discarded, and Caroline found herself looking forward to these mornings with Annie more than those nights with Del.
It takes another year until Annie's plumbing breaks and Caroline walks in on her showering in her downstairs bathroom. Annie doesn't care; she just makes her regular morning conversation and it's this moment that Caroline realizes how much Annie's lack of boundaries means to her.
Caroline meets Annie at Remo's and for once they dine alone and it's only once they're into the main meal that Annie realizes that this is the nicest meal she's had with another person for years. It's nicer than her last ten dates, at least.
Richard leaves New York without a word and Caroline's wedding falls through and Annie's there to comfort Caroline and somehow they end up kissing desperately up against the drafting desk. Neither of them is quite sure how it came to this and they're still bewildered in Caroline's bed a few hours later, buck-naked and sweaty. Still bewildered, that is, until Annie slides her hand back up Caroline's thigh, mouthing her breast urgently. There's a certain clarity that comes with having lesbian sex with your best friend.
Del doesn't find it strange when Annie comes rushing down midmorning, stealing Caroline's coffee and running out the door yelling something about a matinee. He's too worried about remaining friends with Caroline to even notice the marks on Caroline's neck left from the pressure of Annie's teeth.
That night Annie goes over to Caroline's apartment and holds her while she watches sad movies and shovels ice-cream into her mouth. And Caroline, looking back years later, can't honestly tell which of those two nights was better. Because both nights were a part of the start of something new, and no one had ever run their hands through Caroline's hair just like Annie did.
And it is the start of something new, something they kept to themselves for quite some time until Richard is back in town and coloring the comic again and comes home early from lunch one day to find them kissing each other on the couch, hands inside each other's clothing like teenagers. He spreads the word but this is New York City so despite the initial arousal from everyone they'd ever dated, it's not even an issue.
At first they both thought it was just about sex with someone who understood but it quickly became so much more. Some nights Caroline waits outside the theatre door just to walk home with Annie, and when Thanksgiving rolls around again Annie wakes Caroline up at 4am and even makes the coffee so they can (successfully this time) tug a giant balloon Caroline around the streets of New York. She even packs a thermos.
It takes another couple of years, and when Caroline is lying awake next to Annie at 3am one Wednesday morning she realizes that although she hadn't ever thought of this happening, it's happened. She's in love, she's happy and she finally has it all.
