Ben, Danny and Tucker end up in jail when their plans to attend a big Halloween party go awry.

Danny stumbles upon a family secret while planning a birthday bash for Bonnie with Ben, Riley and Tucker.

Riley hosts a cocktail party in order to meet Ross' friends, and Ross tells Ben not to attend. Meanwhile, Danny tries to figure out his new girlfriend's last name; and Tucker starts divulging secrets after he has too much to drink.

The gang reflect on their past entanglements, forgetting to safeguard a cherished item of Bonnie's in the process.

Tucker finds Zoey snooping around his apartment and assumes she is there for him, so he takes it upon himself to ask her out. However, Zoey believes Tucker is setting her up with Ben. Danny finds himself in a similar situation when he tries subtly asking Sam how he feels about Ben, but she thinks Danny is asking her out. And Riley finds herself in an uncomfortable situation when her client tries to take things to the next level with Bonnie. Are there any perfect matches?

Riley is frustrated that Ben only has eyes for Sam and not for Zoey, who she thinks is perfect for him.

As Ben and Riley both realize they are in for more than they bargained for with dating older, more mature adults, they work together to come up with a plan to get out of their respective relationships. When Bonnie and Tucker gain insider information about players on Danny’s hockey team, they bet against the Rangers to win some cash.