How not to be boring on dates

You know boredom = death. You don’t know how to not be boring. “Talk Less. Listen More. Here’s How. Lessons in the art of listening, from a C.I.A. agent, a focus group moderator and more.”

Good listeners ask good questions. One of the most valuable lessons I’ve learned as a journalist is that anyone can be interesting if you ask the right questions. That is, if you ask truly curious questions that don’t have the hidden agenda of fixing, saving, advising, convincing or correcting. Curious questions don’t begin with “Wouldn’t you agree…?” or “Don’t you think…?” and they definitely don’t end with “right?” The idea is to explore the other person’s point of view, not sway it.

Often it’s better to make statements than ask questions.

You also want to avoid asking people personal and appraising questions like “What do you do for a living?” or “What part of town do you live in?” or “What school did you go to?” or “Are you married?” This line of questioning is not an honest attempt to get to know who you’re talking to so much as rank them in the social hierarchy. It’s more like an interrogation and, as a former C.I.A. agent told me, interrogation will get you information, but it won’t be credible or reliable.

In social situations, peppering people with judgmental questions is likely to shift the conversation into a superficial, self-promoting elevator pitch. In other words, the kinds of conversations that make you want to leave the party early and rush home to your dog.

Instead, ask about people’s interests. Try to find out what excites or aggravates them — their daily pleasures or what keeps them up at night. Ask about the last movie they saw or for the story behind a piece of jewelry they’re wearing. Also good are expansive questions, such as, “If you could spend a month anywhere in the world, where would you go?”

Research indicates that when people who don’t know each other well ask each other these types of questions, they feel more connected than if they spent time together accomplishing a task. They are the same kinds of questions listed in the widely circulated article “36 Questions That Lead to Love” and are similar to the conversation starters suggested by the Family Dinner Project, which encourages device-free and listening-focused meals.

These are things players teach guys to do. Many guys are technical, focused on achievement, and blind to most of the emotions/feelings chicks have. Conversationally, many guys see in black and white, while chicks see in full color. Most chicks are not results-oriented, they’re feelings-oriented, so when guys try to talk about whatever they’re learning or their latest achievement, most chicks zone out. It’s even worse when the guy’s only achievement is from playing video games

There are exceptions. If a guy has learned something about dancing, acroyoga, theater, singing, etc., a lot of chicks will be interested in that. Lots of chicks are into gossip, but gossip is dangerous, if you make her think you’re not part of the secret society or are going to judge her sexually. Gossip is also irrelevant from online dates with girls who you don’t interact with socially.

Good conversationalists get that way through practice. If you’re the typical online social ret**d it’s going to take you a while to get there. You practice a little bit every day and after a couple years you get pretty good. Like everything else.

Socially skilled players also know when to break rapport. If she’s rambling on about her family, treating you like a girlfriend, etc., or extensively engaging in long, too-safe topics, it can be useful to break rapport, spike her sexually, etc. Every situation is different and no guy does this perfectly all the time. As usual, Krauser’s textbooks have loads of details on this subject and much more depth than I can offer. I have heard many chicks complain about boring conversations with guys and many guys complain that chicks seem bored and bitchy… rather than blaming chicks for being who they are or blaming guys for being who we are, I suggest pragmatically upping your skills, instead of complaining.