“Do I look fat in this?” “Which should I wear, the red blouse or the white one?” “Do you think she’s prettier than me?” Yep, you know where we're going with this one.

It’s time to get her a gift. Why? Who knows. Maybe it’s her birthday. (In this case, maybe it’s your birthday.) Maybe it’s an important anniversary for you two, like a year since you started to date, or a month since your threesome with her best friend (yeah, right), or six weeks since the first time she ate something off your fork (more likely). Whatever it may be—a legit anniversary or some woman made-up one, she’s made it clear you have to get her a gift. What should it be? Why lingerie, of course. Why would you buy her anything else? It’s perfect! Not so fast, Romeo. Buying lingerie is a tricky business, so pay close attention.

There is a ridiculous notion that men should avoid women with cats, especially when they are in their thirties (the women, not the cats), while it is fine to date women with dogs. Truthfully, it is better to date women with cats than women with dogs. Women with dogs have too many excuses available to them and require extra work.

Every little boy wants to be something cool for Halloween—a vampire, Darth Vader, Indiana Jones… I wanted to be Snoopy. Are you done laughing? Good, because you might just learn a little something, which is, after all, why I’m here; to be your wingman. (But unlike a wingman out with you, there’s no chance I’ll cockblock and take the girl.)