@ErinRosado: If you want to do that, then yes, you have to tell Caraway to beat feet.
Aside from the possible Upton marriage, there’s Yiska, Schmidt, Caraway, Maria, and Preston. There’s also some threesomes:
Caraway/Maria
Caraway/Yiska
Schmidt/Yiska
Schmidt/Maria
Yiska/Maria
You can also arrange Yiska and Maria to get together without you. Note that the only actual threeways are Yiska/Maria and Yiska/Caraway. (For some reason, Caraway isn’t into double-teaming you with Maria…believe me, I’ve tried.)