My friends don't deconstruct dating like I do. One friend told me he just went on dates and the girl suggested on date 3 to kiss (in public). Fast forward a bit and they're together. How does that even happen..? Another guy met a girl through cold approach and I think that it was months until the seduction. And it was a cold approach girl!why don't you ask your friends?
Aside from your poor pacing (even if you took a more "traditional" approach to dating, you still need to consider pacing). You have bad framing, and a lack of leading. Way too passive. No matter how many dates you want to draw the whole thing out over. So fix all that maybe. Maybe if you where this super dominant dude who lead things with gusto, and built tension and intrigue, set the right frames, and called the shots. Maybe you could get these women out over a number of dates. But I wouldn't recommend drawing things out so long. Especially since you are underdeveloped in all those areas
Look man, you have to strike while the iron is hot. That's life. Your best opportunity is in the moment. Not the future.
Why do you want to draw things out so long any way? My theory is that the idea is appealing because it allows you to be passive.
Your god given looks are not your fundamentals
Your fundamentals are the things you can change/work on
Your presence
Your Voice
The way you style yourself
The way you cary yourself
You can't change your good given looks, so you have to find a way to get over it and be confident in yourself any way.
Excuses, excuses
I don't want to move slowly I just want some leeway or insurance that if I mess up a little, the whole thing isn't completely ruined. I can give one solid reason. Last time I was laid was over 3 years ago and she was around 15lb heavier, 4 ft shorter than I am and in the end I tried to friend zone her because I didn't feel any attraction. There was some fallout to handle there ; she of course wasn't pleased about it. She did seem to tell me that she was happy about the lay though, just not that I changed my mind afterwards. But the point is that getting laid seems to give you certain obligations to handle things well afterwards. Also, if I want to meet the woman, go away for a week, fantasise about her, think about her and then go for the seduction, what's wrong with that? What's wrong is that it's bad game and will fail but my point is that some guys could conceivably want to wait until after the first date, if it could be possible. I'm not skilled at all and first date lay adds even more pressure to a difficult situation (the first date itself) for me.
Regarding the excuses about my logistics, I've brought two women back and they felt uncomfortable within 5 minutes of walking in, while she was making herself comfortable and before I sat down next to her. One woman had a fake phone call emergency and the other asked to leave. But I know that you would all rather read about mess ups like this than the lousy dates that I have.
I certainly do have low self esteem. I think that it's because of the awful results that I've had. I've had at least 40 dates since that lay that I mentioned 3+ years ago. I don't see a way out besides actually executing good game and getting some dating successes.