This post has been ranked 10.00 out of 10 with 1 votes.
There are some people with which you simply won't connect very well. Keep in mind that in any conversation between two people those two people will share the responsibility for it to be one they both can enjoy. If you're talking to someone who doesn't care to make the conversation interesting, well..
Anyway, there are some principles you could use if you're into that stuff:
- Successfully convincing yourself that anyone you'll ever meet has at least one interesting thing you can learn from them. I used to be that way when I was about 20, I was opening up anyone I met on the streets, on the tram, busses, wherever, being truly curious what I could learn from them and how they would brighten my day with their stories. A few years later I stopped doing that because a) I was very depressed after the relationship with someone I truly loved broke down, b) I realized that I'm forcing these things even when I'm not into talking and c) I was basically providing all the energy and structure for each conversation while my other conversation partner wouldn't, which became rather exhausting after a while. A few years later I wondered why people had become less interesting and why I had encountered so many interesting people back in the days, until I realized that people are still interesting, I'm just not asking them to be anymore so they seem dull. It's mostly a self-fulfilling prophecy thing, really: if you're not expecting much, you won't be getting much. Same is true for my students as a teacher, when they realized I believed in them for real, they would blossom beautifully.
If you want to have an interesting conversation, direct your efforts at digging up the interesting parts of your conversation partner. Mind that what is interesting to you isn't known to the other one so he'll have a hard time chosing what to tell you to make it interesting, which is why sometimes it's nice to share some of your stuff so your conversation partner will have an idea about what could interest you.
Using open questions related to feelings is usually also a good idea, as long as you're truly interested, like "How did you decide on following that career choice?". Only ask if you're truly interested on the answer, otherwise the conversation will feel very weird to the other one. Ask questions that will best be answered in story form, after you get your conversation partner to tell at least a short story, you'll usually have enough clues to ask further questions that can expand the story. Follow your curiosity and invite who you talk to on a journey through their lives following your questions.
Finally, if you don't feel like contributing a lot, just don't. Silence is a powerful tool in your conversation arsenal if you use it correctly and don't freak out yourself. Just look at your conversation partner silently, spiced with a little curiosity while radiating acceptance towards her. You'll usually get a lot of reactions you can then comment on or (even better) ask new story-seeking questions.
Over the years I've developed a habit of not talking too much to people but being very observant and if I feel like it I will start a conversation with someone which will usually go very deep quickly. In the beginning I have often wondered if people wouldn't see me as weird if I never talked to many people at social gatherings, but I've found that by not being at the center of attention and being somewhat selective in who I chose to talk with and also how long (if I don't want to talk anymore, I don't care much about social norms or politeness, I'll just leave the conversation), my conversation time usually seems to have a lot of value to people and they actively seek me out a lot of times. But I do have a rather unique personality.
By the way, it's been years since I've been on a "date" and I wouldn't want to do it anymore. It kind of sets societal rules on how it should proceed, and I don't like rules that will usually result in predictable outcomes (like your way too logical conversation).