Now living in Florida, Madison spends her first Valentine's Day with Tyler. A confused Connor confides in his mom. Newbie Logan goes suit shopping.

Emma showcases her romantic dreams through song. A shared love of cheesecake sweetens Logan's date. Connor speaks his heart on a picnic with Georgie.

Pricey potatoes and a pesky fly can't stop James and Shelley's dinner. First-timer Dylan is eager to try dating. Emma meets a suitor at the tulip garden.

Connor and Georgie spend their anniversary at the Renaissance Faire. Madison and Tyler explore Nashville. Logan and Hailey share a spooky second date.

Between Logan's first kiss and Emma's crush, is love in the air? James and Shelley go house-hunting. Connor and Georgie see sights and family in England.

Dylan's mom offers him sage advice before his next date. An attempt at voicing his feelings goes awry for Connor. Logan cooks for Hailey and his family.

Familiar faces gather to celebrate Madison and Tyler's big news. James and Shelley spend quality time in Cape Cod. Connor finds comfort in his pals.