Women: Tips on getting conversation "deeper"... or not ?

When I go out with my friends I like and enjoy small talk… and light conversation. Sometimes we talk more politics or current events. We can go on all night and its never dull.

Now when I’m on a first, second or third date… its so much harder to get the conversation going… especially beyond the small talk. I feel the dates are lack luster when we don’t manage to get to know the girl a bit more… but how to “know” more without being intrusive and rude ? I have a serious problem talking about more personal things… or nudging the conversation into something the girl might enjoy more.

Tips ? Topics that are politically safe and might lead to more interesting conversations ? Even better how to get to know the "person" within that female body ? Or avoiding becoming a confidant (=friend=relation death)

What about negative experiences ? What should be avoided that isn't common sense (to men at least) ?  Thanks

Ask the person questions about their hobbies and interests too them. See if they bounce it back towards you asking about you. ( Most don’t do this. Reciprocity is dead.)

After you get a feel for that, go for the hot button topics: Religion, politics and toilet paper hanging under or over.

The same way you get to know any other person, silly. You ask them about what interests them, and you ask questions about that. Talking about hobbies and whether or not they like their job and why might seem like boring-ass smalltalk, but it’s actually quite a good way to get to know the real person. Familiar topics they’re enthusiastic about make people comfortable, and they let their true personalities come through. And even if the true personality isn’t someone you’re especially interested in continuing to see, you can pick up some really interesting tidbits of information in conversations like that.

The simplest technique to keep someone talking is to reflect a statement back at the person in the form of a question. Take the last few words the person said, and repeat them with question inflection.

It isn’t intrusive, and can keep a conversation going for quite some time.

A second technique is free information followed by a reflecting question. If something she says is of personal interest to you, make a brief comment about it, then reflect her statement afterwards. This gives her the option of continuing to talk about herself or to turn the conversation back to you.

Neither is intrusive, but both allow the other person to be free with information she wants to share.

I made a list of 200 random questions from the mundane (If you were a car, what car would you be?) to more serious stuff (Do you have any regrets in your life? If so, what?). I made it into a game and I’ve found that most people enjoy playing. It’s best to do when you are at a home or some place comfortable and have had a bit of alcohol to get the conversation flowing.

There are only two rules: 1. You can’t talk when anyone else is talking. 2. Anyone can skip any question they like.

Most people like talking about themselves and while some won’t answer the deeper questions for a long while, the mundane stuff can also tell you a lot about them.

I manage to have the version of the game I made in high school online. It’s a very early version and I know a lot of the questions have errors or aren’t the best, but you can base yours off of that.

Hi Kaitlyn,

Sorry, socially backward male here. I get your first suggestion:

She: I can’t stand italian restaurants.
He: Oh? You can’t stand italian restaurants?

but I don’t quite grasp your second idea. It sounds like a good technique. Can you illustrate with an example, please?

I think she means an exchange like this:

She: I really like photography.
He: I took a photography class once that I loved. Is it just a hobby for you or do you have a lot of training?

That way, she can answer your question (“I’ve actually only taken a few classes…what kind of photography class did you take?”) or just continue talking about herself. It’s useful because she knows it’s a topic you like and understand so she’ll be more comfortable discussing it.

micahjn got it just right.

Well, hell–there go those dinner reservations…<date ends>