Brian, a 33 year-old playboy, has put walls up after a devastating breakup. This serial first-dater treats dating like a game as the countless women he meets online pale in comparison to his lost love. When he meets a woman who makes him nervous for the first time in ages, he grapples with relinquishing control. Will he be able to give in to a second date and a future with someone new? Ephraim, a 33 year-old single father, carries the weight of raising his young son and caring for his sick father all on his own.

Jason, a 33-year-old film director from Sandusky, Ohio, has dreams of a true Hollywood romance, complete with a Pam Anderson-type for his leading lady. After a string of failed dates with the typical California blonde bombshell, will he follow his friends' advice and open his heart to a down-to-earth girl from the Midwest? Matt, a 27-year-old millionaire, uses online dating to find companionship while on the road for work.

Travis, a 36-year-old virgin, turns to online dating to find his bride. This devout Christian has high expectations. His future wife must be beautiful, virtuous, love the Lord and appreciate his desire to remain a virgin until marriage. Will his rigid guidelines keep love out of reach, or will he bend the rules for the right girl? Davey Wavey, a gay YouTube personality with over 4,000 messages in his dating inbox, has been on hundreds of online dates.