Matt wrestles with his feelings for Eve, and Charlotte convinces him to go to a grief group. Meanwhile, Riley struggles with her own "will she or won't she" about her feelings for Gabe.

Matt and Eve go on their first date but have different ideas of what it should entail. Riley befriends the mom of Georgia's new friend while Carter mediates a tiff between Gabe and Stitch.

When Riley discovers Carter's job pays more than hers, she decides to find her forever career and clashes with Matt over her future. A familiar face drops by Parker Customs, Georgia gets a big surprise, and Matt debates letting go of a piece of the past.

When a raccoon appears in the Parkers' yard, Matt sees a chance to teach Carter a lesson about facing his fears. Meanwhile, Riley struggles to navigate the world of dating apps and goes on her first post-divorce date.

Matt plans to spend Halloween with Eve, but the real terror begins when she wants to sleep over. With Carter and Georgia out for the night, Riley invites Gabe and Stitch to a party, hoping to relive the crazy, epic Halloweens of her past.

Matt's dream build turns into a nightmare when controversy between Stitch and the client threatens to derail everything. Meanwhile, Riley hires Carter at her coffee business and quickly learns that working with family brews more tension than drinks.

This holiday season, the Parkers discover that romance isn't always a smooth ride as Matt and Eve are on thin ice, Gabe enlists Riley to help Amelie impress his mom, and Carter seeks help with his 'promposal'.