I started writing this as a response to a student's question, but it got quite detailed so I thought I'd share it with you guys too!
I had a few bad dates where the girl was kinda boring, stupid, or just not into my humour, interests or outlook. The reason was, back then I was still being way too funny, talkative, and entertaining on the initial approach. Although that sounds great, what would happen is, she would be like "oh yeah he was funny and entertaining, I'll see him for a date why not?" Whereas I'd asked NOTHING of her – I didn't know a thing about her, I hadn't made her invest anything in the interaction, challenge her in any way or show I even gave a shit what she thought – because I spent the whole time talking instead of asking her questions and listening!
So, a bad date is good feedback that although you're doing a bunch of stuff right (otherwise there would be no date to begin with), you need to really make sure to do a bit of qualification in your initial interaction and make sure she's actually the kinda girl you wanna spend a couple of hours with in the first place. Simple questions that start getting to know her and go down the road of qualification are things like:
So what gets you up in the morning?
What do you do for fun?
What about doing X makes it so enjoyable for you?
How does it feel when you do / accomplish X?
WHY?
The point is to challenge her to invest, prove/justify herself, and dig a little deeper to find the underlying reasons and emotions behind why she does what she does and who she is. Not only do you connect much more deeply, but she immediately sees that you are a man with real standards, and she starts to really care what you think about her, and thereby starts wanting to please you.
On the date itself, there is a certain structure you can try if you feel like things are clunky or there are too many pauses that you find awkward. (Although remember, a pause in conversation is perfectly natural, and if you show you're comfortable by staring into her eyes seductively, she'll usually just admire your confidence and be turned on rather than thinking that the pause is awkward.)
The general strategy is to move from the present & specific to the past & general/abstract. (This is why the question "what does 'love' mean to you?" is something that would be natural to ask as you're finishing the wine and sharing a dessert, but very odd to ask as you're just walking her to the café).
So start light, recent and specific. For example, I might tell her a funny story about something that happened to me within the past couple of days, that might segue into our first meeting and something that happened after we walked away, and she might have something of interest that has happened to her since then. I'm also making a connection between the positive emotions she felt after the initial approach and right now.
When you meet her, you kiss her on both cheeks and pick her up and spin her around. This immediately shows confidence, dominance, leading and is sexual whilst being fun, playful and (seemingly) spontaneous. It begins the physical conversation that, for the most part, frames the entire verbal interaction.
When you sit down (or if it's a service establishment, after you've ordered) you have a good 20-30 minutes uninterrupted to chat. (Remember to sit at 90 degrees or next to each other so that you can touch!) This is when you can go more general and further back in time. If you've done your job on the initial approach, you should have written down at least 5 things that you find interesting about her that made you want to meet her again. Now's a great time to bring those up! For example "I remember you telling me you travelled to South America last year – how was that / what made you decide to do that / what was the most memorable experience from the trip / what did it feel like when you saw X place?" etc.
And that's fundamentally the real answer to your question – what you should talk about on dates is HER. People love talking about themselves and if you listen with an open mind, show you're honestly interested, and move the conversation towards topics you're interested in, then you can let her talk her way directly into your bed without much effort on your part!
Don't forget to play the question game. It's great if for any reason you get stuck and feel the conversation isn't going anywhere. Just introduce it by saying "hey let's play this game!" The rules are
1. Whatever is said stays between us
2. You get one question, and one follow-up question if you want it
3. You can't ask the same question back to each other
and that's it!
The great thing about the question game is you can immediately skip ahead to super deep, abstract, personal questions very quickly, because it's a game! So you could start off with something like "what are 3 qualities that are the most important to you in a relationship, whether it be business partner, friend or lover? And why?" This is a great question because it immediately elicits her core values. You can then start to find out a lot about her, and you can start to bring out those qualities in yourself more (if they're at all aligned with who you are as a person!)
During the last 20-25% of the date, it's important to turn the conversation sexual. The question game, again, is like a huge cheat-code for this, because it's a game, you can just skip straight to sex out of nowhere and it doesn't matter!
My go-to question is just "what's the craziest place you've ever had sex?" This is actually a great "sexual qualification" question. Firstly, I immediately find out if she's a virgin (so I can decide whether this is a girl I want to invest that kind of time and energy in teaching). Secondly, I can start to find out if she's sexually open, liberated, is adventurous, and all kinds of qualities I admire. I can also show her, when she gives me her answer, how non-judgmental and open-minded I am about sex. And we can transition into the SNL-friendly workhorse, the "isn't it such a terrible double standard the way women are judged negatively for sleeping with a guy they like" speech. Taking the normal frame of an interaction, and flipping it on its head in a playful way, is pretty much the most awesome thing you can do. It's the basis of all kinds of great humour, it shows you're socially intelligent enough to "get" the frame in the first place, and done in a playful way it's fun for people to jump into the new frame you've set as a part of a little "role-play" adventure. A simple example is taking an innocuous comment from a woman and implying she's hitting on you – because usually it's the woman who gets hit on by a guy she just asked the time from. Women always laugh at this because they're like "oh this guy totally gets it – he understands my reality" as well as it just being humorous.
What I do on dates is I flip the standard frame of "guy pays for everything, entertains the girl and essentially auditions for the part of her next provider boyfriend by trying to display as many qualities he assumes she wants, whilst she essentially sits there looking pretty, takes notes and makes a decision whether or not he's allowed to touch her up later." The way I do it is by instituting the "points game" very early on. I might even do it over the first few texts, e.g. "if ur late I'll deduct 1 point for every minute
" On the date itself, if she says something I disagree with, or something stupid, or anything I might wanna break her balls about, I just mime getting out an imaginary notepad, and then speak "oooh that's gonna cost her another 2 points" give her a cheeky smile and put the notepad away. I have never gotten a negative response from doing this, because it's just a game, it's not serious – I'm not really calling her out on anything. But what's happening is the underlying frame is "she is working for my approval and I'm taking notes. She better not fuck it up too much!"And that's the frame you wanna come from on dates, and in general with women you're interested in having a relationship with.