A/N: I wrote this forever ago for Leigh-Kelly's 5 year Brittana challenge on Tumblr. This is a one shot because I don't feel like continuing this very canon story with very canon characters. Oops. Enjoy!

February 19th, 2020

Santana isn't sure how Brittany got her to agree to this. All she knows is that they're not going to spend their anniversary in Lesbos this year, and she isn't happy about breaking that tradition at all.

February 2015

"I can't believe we have the same anniversary now" Brittany wrapped an arm around Santana as they walked out of the auditorium with Blaine and Kurt.

"I can't...wait, hold up WHAT WAS THAT?" Santana looked up at Brittany, who was happily smiling.

Brittany continued "Yeah you guys, we're in this together now. Okay? You can count on us. And I think we should make a pact to celebrate our anniversaries together every year for the rest of our lives."

Kurt laughed "Or maybe every fifth year?"

"Okay, fifth year." she relented, and Blaine and Santana reluctantly agreed as well. As soon as the boys were out of earshot, Santana gave Brittany her signature "WTF" look.

"Britt! I don't want to celebrate our biggest anniversaries with the gays!" she crossed her arms, and tried to pout.

"It'll be fun San, please?" Brittany pulled off a pout, and Santana groaned before agreeing and kissing away that pout.

"Now, let's go to the Bahamas!" Brittany smiles, pulling Santana to the car.

2020

"Why exactly are we not just staying in the city and spending the day with them?" Santana asked Brittany for the millionth time as she pulled their suitcases from the taxi trunk.

"Because" Brittany paid the cabbie who sped off "I still want our anniversary to be fun."

"Hawaii with the gays, who are going to call Rachel every hour about her surrogacy sounds like fun to you?" Santana grabs Britt's hand as they make their way into the airport. Brittany smiles and nods.

"Where are they anyway? Wouldn't it have been easier to meet at one house and share a cab?" Santana shows her ID to TSA watching Brittany do the same.

"Well yeah, but this is more fun. They're already at the gate, Blaine apparently thinks Starbucks is best at the airport." Brittany said, tossing her shoes in a bin with Santana's.

"Well I think an extra hour in bed with you on our anniversary is better than any coffee" Santana kissed her lightly, retrieving their shoes.

"Totally worth it." Brittany agreed, grabbing hold of Santana's hand so she wouldn't get lost in the airport. Brittany only let go when she saw Kurt and Blaine, running to hug them. Santana dragged her feet, catching up and side hugging the other couple reluctantly. Blaine offered to buy her coffee while Kurt and Brittany reminisced about the one time they'd dated and she gladly agreed.

"You don't seem excited. Hawaii is beautiful and quiet this time of year." Blaine paid the cashier for Santana's caramel latte.

"If it was just me and Britt I would be. No offense, but I like to keep our anniversary just for us." she grabbed the coffee, taking a couple gulps.

"None taken. I wasn't thrilled either, but Kurt reminded me that we agreed, and that he was actually looking forward to it." Blaine rolled his eyes, casting a look at the other two giggling.

"Same here. She hasn't stopped talking about it since our honeymoon ended years ago." Santana played with the large diamond on her finger.

"That sounds like Brittany. How are you two doing anyway? I know we talk frequently, but you two seem like you are in the same place you were five years ago." Blaine took a seat beside Kurt who had Brittany preoccupied with a video of a new Broadway dance number.

"We are great. You know I passed my LSAT and I still sing every once in awhile at clubs." Santana said "And Britt's studio is booming, she loves the kids, she loved the day you two visited." she smiled.

"But that's your career. Haven't you two thought about starting a family? Kurt and I are so excited for our bundle of joy." Blaine nudged her.

"Yeah, we have. We just don't know who's going to put their career on pause. I keep telling her that I should do it, since I'll be able to work longer and from home, but she's really adamant that she can take time off." Santana sighs "I don't think she realizes that it could have a long term effect on her."

"I do." Brittany said, kissing Santana's cheek and frowning "I just don't want you to do it just cause your career is more flexible. What if you miss a huge case that could make or break you?"

"There will be more. I promise." Santana squeezes Brittany's hand "What do you say, we start trying when we get back?"

"Yeah…okay. But if you carry this one and we want another, I'm carrying number two." the blonde insisted.

"Deal Britt." Santana kissed her.

"Hawaii, here we come!" Kurt screamed as the overhead announced it was time to board.

"Happy Five Years Everyone!" Santana said.

"Happy Five Years!" the other three smiled.