Andy (Steve) is the new pet project of his Smart Tech co-workers -- David (Paul), Jay (Romany), and Cal (Seth). This is no small undertaking as Andy’s most exciting evenings are usually spent watching Survivor with his senior citizen neighbors and admiring his action figures, including Aquaman and his 47 GI Joes. But the guys, armed with all of their worldly experience, are determined to help Andy lose his virginity at the age of 40.

Of course, his new buddies’ advice is pretty flawed based on their own unstable relationships and extremely unhealthy opinions about women. Still, it’s the best offer that Andy has so he dives in subsequently finding himself in some pretty precarious situations. While the guys are focusing on getting Andy laid, the latter meets and falls for Trish (Catherine), a quirky 40-something grandmother who owns a “We Sell Your Stuff on Ebay” store across the street from Smart Tech. Unable to tell Trish his secret, Andy happily makes a pact with her that is sure to hide his virginity for a bit longer.