Okay, I’ll have to back it up a bit. What makes us anxious? Being in situations that we don’t feel we have control over. The biggest uncontrollable thing there is! And that’s not going to change. My point is, when you are doing something outside your comfort zone, aka growing, it’s going to feel awkward and uncomfortable. And that’s okay. That means you are pushing yourself. Now, what can help it? First, repetition. It’s as simple as that. I tell my clients, “Like tennis, I’ll teach you a forehand, then it’s your responsibility to go out and hit 1000 balls up against a wall.” It’s not going to go well every time. Not statistically possible. But make sure with each one, you have a take-away. What did I do right? What can I do better? Second thing is goal setting. Set your goals small. Not saying lower your standards at all. I’m saying, don’t go in with a thought that “I’m going to have a long conversation/get a number/make out with that girl I want to talk to.” It’s too big a goal. Set small ones, like find out what the best restaurant in their hometown is. Or just that you are going to ask 5 questions. This will 1) help you focus on a goal and reduce your anxiety about what to say next and 2) make your goals achievable which makes you want to practice more. As you get better, like a weightlifter slowly adding weights, you up the difficulty level. And understand, like that weightlifter, every new level is going to feel difficult and uncomfortable. But like I said, that’s growth. To your second question, the simplest answer is listen to her. I mean really LISTEN. This isn’t to say don’t talk. What I’m saying is, if she says, “I took a jazz cruise down the Seine river in France” you can now bring up music (How was the jazz? I’ve always wanted to get into that but I’ve always been more of a new wave guy. Do you know The Cure?), boats/water (I’ve never been on a river! But we used to vacation on a lake in the Poconos. It’s so great to be around water!), or travel (Lucky you going to France! That’s always been my dream place. Where else would you like to go?) When they talk, they are giving you all the clues about their interests and what they like to talk about. Again, as with the approaching, the more practice/practical application you put in, the more results you’ll get.