Long time lurker finally started going out more and employing what I have been studying. I have had two occurrences that have been strange to me and I haven't heard anything about people having similar experiences so I am looking for advice on what I am potentially doing wrong.

On Saturday I went out with a few friends to watch the fight, while at the bar I noticed the waitress, and since I was trying to be the center of attention (had literally half the bar knowing me and buying me drinks) she noticed me. We exchanged glances and I gave her my number and told her to text me when she got off. Flash forward a few hours I am at the Casino as I am about to leave the waitress shows up and I end up staying a few more hours at the Casino. We talked for half the night, I escalated kino and eventually ended with a K-Close (had a few things that I wanted to work on like talking about myself too much and not escalating fast enough, and not making my intentions 100% clear but in the end successful night).

Sunday I end up talking to her through text and we decide to hang out again on Monday.

Come Monday we go out, get ice cream and then go to the driving range. I decide to double back on the things I thought I fell short on earlier in the week. Night continues and eventually she invites me back to her place. We bust out a bottle of wine and sit on the porch while talking about some crazy things we have done in our past. After a while I get the line "I don't understand you, you're not like any guy I have talked to before". If you want an ego booster that is the line that will make it happen.

The night continues and eventually I say we should go inside and watch a movie (the porch had lawn chairs so it made it difficult to kino). She agrees and we go inside, we continue to talk and I start to move in for another escalation. Now here is where things go south.... She starts talking about her past and her regrets, I haven't had this happen before so I start to panic. I make multiple attempts to drive the conversation away from her talking about that since I don't want her to associate me with them. Ultimately I fail miserably and get about 30-45 minutes of hearing about where she thinks she made mistakes in life. At this point I notice she looks down so I figure I could probably earn some points with some empathy. So I try to console but I also notice she has gone cold to me now. She isn't receptive to myself touching her but doesn't deny the motions either. I am not sure what to do at this point so I look for an opening to leave (luckily it was 4 am so an excuse was made easily) and head out. On the way out I go for another K-close which she doesn't stop me but she also doesn't seem into it either.

On the way home she does text me and tell me that she had a lot of fun and that she can't wait to hang out again...

So at this point I am confused on what I am doing wrong. This isn't the first time the situation has happened to me and I still have no clue how to approach what to do when that happens. Does anyone know where I should fix my game to avoid these subjects? Or ways to get out of them once I am placed in them.... Also is this person worth continuing to persue or are have they already rejected me?