Poindexter is Gizmo's older brother, close friend of Shining Armor who went to high school with him, and along with 8-Bit and Gaffer, he's the reason that Shining Armor and Cadance ever got together in the first place. So he's pretty close with his old high school friends. He's still a massive nerd (and don't tell anyone this, but so is Shining Armor) and he still plays Oubliettes & Ogres with him, along with the rest of the old crew and their families, and unbeknownst to the general public, Shining Armor's daughter Quartzy. She's a bit embarrassed by this fact, and has been known to deny it vehemently, but he taught her everything she knows about O&O.
He's married to, and cross his heart and swear to fly, Pinkie Promise, a real life secret agent. No, he's not joking. No matter how hard you keep laughing. Her name's Tealove. A certain agent Sweetie Drops can totally back him up on this, but that would be breaking the whole secret agent deal. Well, regardless of the veracity of the secret agent portion, Tealove is his wife, so… yeah. Hot lady and the nerd; it happens. Even if the nerd is a crossdresser. I feel like this quote may be apropos. Crossdressing and heterosexuality are not opposites.
Seriously though; he looks goddamn great in this ensemble, don't lie.