For June Bailey, life is all about meeting outlandish requests for her billionaire boss which includes keeping an eye on the woman's artsy, nomad nephew, Tucker Frost. June highly underestimates how difficult spending time with Tucker will be. Between his good looks, irresistible charm, and a way of helping her see the beauty beyond her check-list life style, she begins to lose herself in more than just his artwork. However, when the time comes for the wanderer to drift away once more, will their love be forced to comply with traditional goodbyes or will it be allowed to exist in freeform?