Greg and Amelia realize that they've only really slept with each other, so they agree to open up the relationship in the months leading to the wedding. In effort to be safe and respectful, they set up six rules to abide by while on their escapades.
Greg goes on a date with Joanie, who may or may not have some kind of contagious illness. Greg must tread lightly in order to avoid breaking any rules.
Amelia goes home with an intelligent and charming young bookstore clerk, but is he really what he seems?
Greg gets some solid advice from Duke and goes home with the bartender. This girl likes to rage. Will Greg be able to keep up?
Greg and Amelia venture to Washington Square Park to cat-call NYU students. Amelia finds Beard, who invites her to attend a rally with him. Amelia hopes that this "date" will lead to a cozy and sexy bed, but does that even exist?
Tensions are high after numerous failures. Frustrated, Amelia goes wandering the streets in search of a ready and willing penis. What she finds may be more than she bargained for...
Greg serendipitously meets a young lady at a coffee shop who shares his taste in Sci-fi. Greg knows that this one is special, so he immediately sets his "Seal the Deal" timer. The fact that they get along so well should bode well for Greg, but will he really be able to seal the deal in 12 hours or less?
Greg and Amelia enlist the services of a therapist to help deal with the stresses wedding prep has put on their relationship, but Dr. Meaney has other plans.
Greg and Amelia consult a wedding planner duo and uncover personal drama that might get in the way of their professional duties.
Amelia is skeptical at first of Greg's choice of vegan wedding caterers, but quickly falls for flattery.
When Greg and Amelia land a dinner date with a swinger couple, they think their dry streak is as good as over. Too good to be true? Spoiler alert: no duh!
Amelia gets unsolicited advice from her mother and sister who, once you meet them, make Amelia seem like a pretty decent person you could spend time with.
Unhappy with their previous set of engagement photos, Greg and Amelia hire a photographer to re-take them. What happens next has a lot to do with horses for some reason.
A young billionaire with a reputation for sexual deviancy based on rumor and hearsay approaches Greg and Amelia for an erotic tryst, believing that they, thanks to Greg's erotic fiction blog, are kink dynamos. What follows is a classic game of "I thought you were the one who knew how to use this sex toy."
Greg and Amelia head to Cape Cod for little vacation and to visit their old buddy Duke Mailor, but end up sorta killing a guy.
The Pioneers will begin streaming Apr 06, 2017.
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