Kyle Cooke is a "man-olescent" at heart and while he is perfectly content with being the life of the party, he is also a successful entrepreneur. After proposing to Amanda after a rollercoaster of a summer last year, he’s now struggling to build their relationship back up while juggling new challenges: settling into their new apartment, wedding planning, and launching a new startup, Loverboy. To complicate matters, Kyle's new business partner in this venture is Amanda and she still has a full-time job. Heading into the summer with new sources of stress, there's more pressure than ever before, and Kyle fears their relationship might be on the rocks yet again.