3) I’ve tried just speaking whatever comes to mind, but it tends to just dwindle into a lot of casual comments and it has the same drawback as method #1 (which is I get short answers and have to talk even more to make up for that).
There’s a lot to be said for observational topics, but only a) if it’s not obvious that you’re desperately casting about to find something to fill the silence with and b) you can use it to springboard to an actual conversation. Personally, I like people-watching; you have any number of ways of segueing into new subjects – fashion, lifestyle choices, even just commenting on their actions. I saved one date from a painfully awkward “what do we do now” moment followed by a good-night handshake by starting running commentary about another couple that was VERY clearly on a first date and using it as a parallel to our own. The trick is to bring the conversation to a place where the two of you can learn about each other.
Also: if all you’re getting are short, clipped responses, odds are that the person you’re talking to is just not that into you. Odds are good that she’s just trying to run down the clock until the social contract says that she can leave without causing offense. The more interested a person is in you, the more they’re going to have to say and the more they’re going to show interest in what you have to say.
4) I’ve tried the chode way of just going interview mode on her, asking questions as well as answering hers. I’ve even tried being genuinely interested in what she says, practicing active listening and all, but in the end it’s just an exchange of questions going back and forth. BO-RING.
I have nothing to say here. I’m just going to pause for a moment and just marvel at the idea of “being genuinely interested in what she says” as a desperation tactic.
5) I live an interesting life and supposedly that is supposed to be the source of anecdotes you can tell people or the relations you can draw between what women are telling you and what you’ve previously experienced, but I don’t feel this way at all. As soon as I have done something, I don’t think about it anymore. I don’t feel a need to tell people about what I’ve done. There’s nothing interesting about having gone skiing, surfing, hiking, clubbing etc. What am I supposed to do? Chime in and go “Yeah I went clubbing too last weekend too! A drunk guy puked on me.” I’ve tried every imaginable variation of relating to what she’s saying, and there’s nothing interesting I can respond with. DOU-BLE BO-RING.
Well here’s your problem: you don’t seem engaged in your own life. If you’re living an interesting life, then why wouldn’t you think about the things you’ve done after you’ve done them? There’s more to an interesting life than just going down a checklist of “cool” activities – the point of collecting experiences and memories is to experience them and share them with other people afterwards. And you can’t do that if you never think about it again afterwards.
It’s about more than just having done something; it’s about how it made you feel and what it made you feel. To take an example from my life, I visited Cambodia a few years back and got a chance to do things I never thought I’d do, including exploring a ruined temple in the jungle. What I took away from it was more than just “yup, that was cool,” it was how humid it was in the jungle and how loud it was thanks to all the birds and insects. It was about feeling as though I was walking through every single adventure fantasy I had watching Indiana Jones as a kid and trying not to yell “Throw me the idol, I throw you the whip!”. It was about the way my stomach contracted and my nuts crawled up into my abdominal cavity when I realized that I’d walked into a live minefield and had to pick my way back very fucking carefully. It was about characters, like the little Cambodian urchin who kept trying to engage me in conversation and sell me cheap crap when I was busy trying to flirt with a cute backpacker while watching the sun set from the top of a ziggurat.
Now granted, this is a bit of an extreme example. Not everything has to be an epic tale of adventure and danger in exotic lands in order to be interesting. The seemingly mundane can be interesting, even enthralling if you sell it properly. This means being in touch with yourself and willing to share it with the person you’re talking to.
5b) Even though my life is full of events, not every activity is going to result in an interesting anecdote. In fact, I feel like they never do, and if they do, it’s only something mildly entertaining. I’ve also read that even if your stories aren’t that interesting to you, you can still deliver them with passion. I find this to not be true at all. Even if I convey an experience with both emotion and passion, the other person still won’t have much to say about it and you’ll be left with an “oh cool” or just another question fired back in your direction since she doesn’t have anything to say about your story.
It doesn’t always have to be about X thing happened while you were doing Y activity with Z.
To use one of your examples: let’s talk about skiing. If there’s nothing exciting or interesting about skiing, you’re doing it wrong.
Now, maybe there was something crazy that happened while you were on a ski-lift or you watched somebody have an epic wipeout. But let’s say it didn’t last time. What do you talk about then? Well, to start with, what is it that you like about skiing? How does it feel to be rushing down the side of a mountain with a couple of planks strapped to your feet and the only thing between you and sudden death is your ability to shift your weight? Do you like carving trails in fresh champagne powder, or do you prefer hurtling over moguls. Are you a moderate skiier or do you like taking on double black slopes? Or perhaps you like the effortless gliding of cross-country skiing, the silence of the snowy air and the way that you almost fall into a meditative trance while you’re traversing a field or forest.
Even the example you mentioned about going to a club and somebody getting drunk and puking on you is potentially a funny anecdote to share if you know how to sell it. Build the tension by describing what was happening before you got puked on and how you saw this person headed your way.Create characters – sway back and forth when you’re describing how the drunk walked, speak with an exaggerated slur. What happened afterwards? Did they fall over? Get ejected by the bouncer? Offer to buy you a drink then stumble into a crowd of onlookers?
So that about sums it up for what I’ve tried up until this point. In order to give you an idea of what I’m working with, let me also give you a personal example from last weekend:
And now we enter into Post Mortem territory. I’m going to break some of this down for the other readers – who would get some benefit from it – as well as pointing out where you dun goofed.