How to have fun/interesting conversations?

Try and see if gambling works: Go straight for some really interesting questions, such as "What's the weirdest thing about you?" and if the person you're talking to isn't taken too much by surprise, it could spark interesting conversations. Do remember that you'll probably get asked the same question, in which case you don't have the luxury of avoiding it.

If you are referring to small talks, I think if you come out more interested on the other person, rather than focus on whether they would like what you would say, I think it will reflect back. People usually like people who likes them. Or think of conversing as giving a little bit of yourself to the other person. Which as I like to put it, letting them in on your quirks. It can turn out to be fun if you think of it that way. When you walk away from a conversation, if there's anything you should regret about, don't let it be "I could have said this instead, that's definitely better that my boring response." Things that could've left the other person feeling better than when you found them or prior to the conversation, those things maybe it's more worthwhile to feel kind of bad about. Hopefully it will make you be a better next time on another conversation. Also, get used to silences when you are talking with another person. Don't overthink what they're thinking. At the same time, don't jump into responding faster than before you could process what the other person just said. So I would say, it's almost always about being a better listener. Maybe if you think about why you are having this conversation, then it would ease up your mind against superficial results. If you came to talk to enjoy the other person's company, then enjoy the other person's company. If you came to talk to make them like you, well.. as someone else has put it on this site, that is outside your control. But if it's about convincing them about something you strongly believe about, maybe a little bit more preparation is required with that. Goodluck.

I'm not sure what you mean exactly when you say "conversations turn into interviews", but asking questions about each other is just a way of finding something in common between the two of you directly. Never expect a conversation to get interesting with some cool questions, that rarely happens. Trust me. Just be original and don't worry about impressing the person. Speak what you want to say and not what you think they want to hear. Be a good listener. Look into the person's eyes at least 60% of the time they are speaking and avoid fidgeting with anything around you. You'll probably find yourself getting more involved in the conversation that way. Don't let awkward silences get in the way and just for the sake of avoiding it don't just say anything random. Plus, if you don't like conversations, why do you want to participate in one so bad?