I'm in my mid-30s. My social development was screwed up because I was homeschooled and isolated while growing up. I spent the majority of my 20s learning how to make friends and stop being creepy. I fell into the Nice Guy pattern and wound up being a wonderful friend, but the girls I was interested in weren't interested in me.

I've improved a great deal over the past few years, but am not quite where I want to be. One thing I've noticed lately is that I can get into a conversation just fine, but it's like I get stuck and don't know what to do if it goes on for longer than a sentence or two.

I've been working on approaching strangers just to have casual conversations, so that I gain practice and the approach anxiety dissipates when I find a girl I really want to talk to. The issue is that if the person I'm talking to responds with anything more than a polite response, I freeze up.

Scenario 1: I was at Starbucks and the barista had a really bright, vibrant tattoo on her forearm, so I commented on it. It was clearly something she was proud of, and she started talking about how she had recently had it touched up.

I've been reading seddit long enough to know that this means I should continue the conversation by talking about related topics. I could ask the meaning of the tattoo, or where she got it, or who touched it up, etc. However, there was a woman behind me waiting to order and I felt like I couldn't monopolize the barista's time. I felt pressured to end the conversation, so I just kept saying "Okay" until she stopped talking.

Scenario 2: I was at the gym yesterday, lifting weights. A pregnant woman was there with her friend doing squats at the squat rack. I had never seen a pregnant woman lift weights, and thought it was cool, so I commented on it. I asked how long she could continue to lift weights, and she said that she could keep lifting as long as she felt comfortable with it. Her friend spoke up and said something, but I felt like I had to end the conversation immediately, so I said something else and walked back to where I was lifting weights to continue my workout.

I'm not sure why I keep doing this. Any suggestions?