[Yeah, the headline ain't so clever, sue me.]
Good conversation doesn’t come naturally to many men. Shyness and fear are the two obvious barriers to good conversation. To help overcome that, I always recommend the website Succeed Socially (link below). The other barrier is knowing what to say and when to say it. This is not easy. Social interaction isn’t always like a soap opera. There are some things to keep in mind when talking to people – women, in particular – socially.
Be outcome independent. This is a core competency of Charisma and the foundation of good social interactions with women. No matter what the level of attraction to the woman you are speaking with, an agenda shouldn’t be percolating in your mind. If your conversational skills are only average, that agenda can absolutely ruin the interaction. Worse, you’ll come across as creepy. The agenda can kill comfort.
Ask questions. The standard Charisma advice is that a confident man makes statements and doesn’t ask questions. The exception to this advice is when a man is simply having a social conversation with a woman who hasn’t yet revealed any attraction to him. The questions should be about environmental things: “Have you heard about that new restaurant that just opened?” Don’t ask personal questions to someone you just met! Shallow questions are good for establishing comfort because they are non-threatening.
Listen well. Take an honest interest in what the woman is saying. You may not like what you are hearing but such is life. Try to remember what she is saying, even if it’s trite and silly. If you want to want to shift the subject matter (I hate celebrity gossip, too), here are a couple of phrases to use just before you change the subject: “That’s not my style” or “I’m not into that”.
Use eye contact. Look her in the eyes once at least once and awhile. This doesn’t mean trying to hypnotize her or looking at her eyes long enough for her to break away her own eye contact. This means honestly acknowledging her presence means that you take her words seriously, even if she’s prattling on about something inconsequential.
Pay attention to body language. Everyone shows their mood and emotional state during a conversation with their body language. This is where a good book comes in (link below). Always be aware of body language, yours included.
Reveal little. The downside to confidence is self-absorption. It’s manifested during social interactions when a guy only talks about himself. If a woman is totally smitten with him, that’s OK. But let’s not forget the woman’s unspoken rule about intimacy (link below), before she’s intimate with a man, she’s looking for reasons to reject him. That means that every personal detail that a man reveals about himself is another potential reason for rejection. The corollary to this is not to monopolize the conversation.
If you can, use humor and wit. This doesn’t mean become the accidental entertainer (link below) and trying to keep her laughing all the time. It means tossing out a funny comeback or remark occasionally. There is a warning here – humor is subjective. What you might perceive as funny might come across as creepy or offensive to others. By listening carefully, you should be able to gauge her sense of humor. For those who are humor impaired and need examples of how a funny conversation should flow, watch TV sit-coms, seriously. Pay attention to timing and delivery. It can be successfully emulated.