How many forced conversation restarts is too many?

So I’m a 35 straight guy and recently I’ve been getting a more instant contacts from dating apps. Meaning as soon as they match with me they send me a message first. I have no issue with that other than it occasionally prevents me from being able to open with a funny pickup line or ice breaker. The issue here is that time and time again the conversation goes nowhere fast. I’m not sure if I just suck at conversation, or maybe they didn’t really want to talk after all, or maybe they’re the ones that suck at conversation. I feel like I’m doing my part to participate. I ask questions, acknowledge responses, ask follow up questions, and just generally try to stay engaged with the conversation but I’m frequently left with a reply that is something like “lol”, “yes”, “no”, “cool”, “not really”, or “That’s awesome”. That’s it, no remark or question or follow up of any sorts on their part. So naturally I assume they just don’t want to talk about that particular subject so I go back to the well and try another one to spark their interest. Again I’m meet with a dead end reply. I’m not randomly dipping into the well here either. I ask them questions like “what are you into” and those are the topics I try. I mean they said they are into them so they should enjoy talking about them, right? Still I’m met with dead end replies the majority of the time. So I shift gears and say well maybe they want to know what I think on the subject instead of talking about themselves. For instance if the topic is music and I’ve been hit with a few dead end replies then I will make a comment about what type of music I’ve been listening to lately with the (what I think to be) pretty obvious expectation of a follow up question from her so that I can talk about myself since by now its clear she’s not comfortable talking about herself. Still more dead end replies. How many of these dead end replies and conversation restarts do I go through before I just give up and move on? Am I the problem here? I have a very methodical approach starting conversations with new women that prior to my marriage (divorced now) was fairly successful I like to think but maybe it’s too clinical now? That being said, it’s not like I’m going after a younger woman. I know I’m only a shadow of what I was 15 years ago and that I should expect diminished returns but I never expected them to be this diminished.