He's So/She's So Trilogy Series by Kieran Scott

When having money is all that matters, what happens when you lose it all? Perfect, picturesque Orchard Hill. It was the last thing Ally Ryan saw in the rear-view mirror as her mother drove them out of town and away from the shame of the scandal her father caused when his hedge fund went south and practically bankrupted all their friends -- friends that liked having trust funds and new cars, and that didn't like constant reminders that they had been swindled. So it was adios, Orchard Hill. Thanks for nothing.
Now, two years later, Ally's mother has landed a job back at the site of their downfall. So instead of Ally's new low-key, happy life, it'll be back into the snake pit with the likes of Shannen Moore and Hammond Ross.
But then there's Jake Graydon. Handsome, wealthy, bored Jake Graydon. He moved to town after Ally left and knows nothing of her scandal, but does know that he likes her. And she likes him. So off into the sunset they can go, right? Too bad Jake's friends have a problem with his new crush since it would make Ally happy. And if anyone deserves to be unhappy, it's Ally Ryan.
Ally was hoping to have left all the drama in the past, but some things just can't be forgotten. Isn't there more to life than money?

Ally Ryan, come on down to the Jersey Shore and forget your troubles!
Have you recently been humiliated in front of your friends and family at your former best friend's birthday party? Was your almost boyfriend partly responsible for that humiliation by withholding some vital information about where your estranged father is? Did you come home to find said estranged father sitting on your stoop?
If so, then it sounds like you could use a vacation! The Jersey Shore is the place to be. Your mother may be living with her boyfriend of only a few months, but at least the stunt Shannen pulled has put some of your friends back in your court. Even so, you're still angry and what better way to get over Jake than to blow off some steam with local guy, Cooper? People will hardly recognize your new attitude, but the old one wasn't getting you anywhere, so who cares!
Jake Graydon, an exciting opportunity is waiting for you in the service industry!
Are your grades so low your parents have grounded you for the summer? Did you the girl you really like unceremoniously leave you behind? Would you rather eat dirt than see your friends again? Then a job at the local coffee shop is just the ticket! Surprisingly, Ally's father is the new manager so you get to be reminded of her nearly every day. Maybe it's time to start flirting with your best friend's ex or even taking school a bit more seriously. Especially when you finally see Ally and she's hanging around with some loser and it's couldn't be more clear that she is over you.
Have a great summer!