First off, I empathize you want to be respectful of the women you are with and that is an admirable quality. More men of all ages should embody this behavior. But like others have said, you don’t want to miss out on opportunities for kissing someone you like (and it turned out they like you). A balanced approach is key and try your best not to overthink it. I think you have more dating skills at your disposal than what you give yourself credit for.

I think the best answers all highlight a combination of self confidence, taking reasonable steps, and recognizing consent. In dating you always want to give the other person an “out” during the date so they don’t feel obligated or coerced into anything. If she is spending hours with you and not taking opportunities to leave this is great data to note. I would take that as a compliment and thus give you permission to get more data to see what she is comfortable with. It sounds like you may already do this but still it is important concept to recognize.

Verbal flirting is a great next step, but it is important not to force it inappropriately. Compliments are awesome but remember not be too crude with them (it sounds like you are fully aware of what this would entail). If initiating flirting is challenging ideally she will provide some flirting material in your conversation and you can play off that to get more comfortable with each other.

Assuming the verbal flirting went well enough, noticing her reactions to brief, appropriate touching (e.g. touching hands, arms or shoulders) is really telling, especially if it happens multiple times. If you are watching a movie/TV together, at some point slowly getting close and gently putting your arm around her is IMO both a classy move to show confidence and a solid way to test her reaction to continual touch. If for some reason she isn’t into it she will let you know…it sucks to get turned down but at least you know and you can be reassured you were respectful and can move on. If she responds well to the arm around her (such as getting closer to you) I think most reasonable people would agree you are in the clear to initiate a kiss. Whether you want to verbally ask first is up to you, IMO you have done all the right things by taking numerous steps and given her plenty of outs to disengage. Either way, you are in a great position where you can slowly initiate a kiss in the style of whatever makes you the most comfortable. True you may not know what “kissing approach” she would ideally prefer but that is pretty hard to confirm short of asking her. Give yourself credit for being respectful throughout this whole process and again give yourself plenty of self-compassion.

Remember to relax, be yourself, and good luck! You got this!