Long-ass post, beware.

Hey there. I've been "in the game" for a few years now but I've never faced a situation like this before, so I'm a bit confused on how to proceed.

Preface: I'm 19, fucking 31-year-old neighbor. I'm focused on myself, keep myself busy, and put myself first (as we all should). She has low self-esteem, a kid, and mental health issues, but hey, she's a solid 8 so it's cool to keep her around. We've been going on dates for a solid month now, and she's slowly getting attached (she told me she obsesses over me and that it's painful when I leave-- although she tries to hide it).

The sex is great, and for once doesn't feel like a damn chore... she makes sure I'm taken care and vice-versa. She's been abused in the past so getting her out of her shell was a bit of work, but now I'm seeing her true colors and it's great. Honestly, I haven't felt this "valued" in a fucking while.

Every week and date before last nights' was great-- fun activity, deep conversation, playful tones, made sure to lead, all that good stuff. However, I'm pretty sure I messed up last night.

Yesterday, I felt like taking her out and so I shot her a text letting her know I'll pick her up at x time to go out. I picked her up with no idea where the fuck I was taking her since I was out all day and didn't plan it out (mistake #1?) and decided to go on a walk in the downtown area. She knew the area better than me, but I didn't let her guide (mistake #2?). Obviously, this pissed her off a bit as it took me longer than necessary to find parking, and a specific area I was looking for (she knew where it was and was trying to tell me where, but I ignored her remarks and thought I knew best) (mistake #3?). In the end, we got there and were vibing, and then went off to the shore.

This is where shit happens. She mentioned how she felt "closed out" the entire date and that she didn't feel like she was with me, but rather she was just a puppy following me-- although I had no clue where I was going (I was trying to be spontaneous lol). She also mentioned how she has never felt this disconnected from me and it felt as if she was hanging out with her friend rather than me-- Although the last few weeks have felt super connected for her. By this point, I knew I had messed up, but didn't wallow, and instead firmly admitted that hey, you know what? I did have no clue where I was going. That's on me.

And that's where the "more input" comment comes in, as she said something along the lines of "I love it when you lead, but sometimes it's too much. Like, you didn't even let me know where we were going so I had no idea how to dress". Is this a result of me not planning out the date, or is it something else?

So-- Should I plan out dates in advance and not do "spontaneous" again, or is this really about not her having enough input?

That aside, I don't want to make a separate post, so a few things that I've wanted some input on how I handled it:

I do intermittent fasting. During the date, she asked, "when did you last eat?" and I mentioned something like 7 hours ago, and she gasped and said you should eat. I was like no, I'm not hungry, I'm intermittent fasting to keep my weight where I want it to be. Then she shot back with "you don't realize how thin you are, you have like no fat", and I was like yeah, so? I'm happy with how I look and I'm able to look at myself and be happy at what I see with where I'm at. After that, she kept pushing the topic, but I kind of just ignored it as I had already made my point.

She brought up how "I don't care enough" and "seem emotionless", and that she wishes I was more expressive-- and I said that's just the way I am... our "languages" are different and we express things in different ways. She then brought up the "obsessive" part and how she's scared of getting too attached to me and I was just like, just do you. Then the point of having a great date and not talking for days came up, and I said that hey, I have a busy life, I don't have that kind of time to be texting you that much... that's why I always end convos with "I'm available during the evening for an in-person" instead of just texting all day... cuz I got shit to do. I also mentioned that when she gets her shit together and gets a job and back in school she'll be the same (she's worried about not seeing me so often) and that it's perfectly normal to not be in touch all the damn time as life comes first.

During the date, sometimes my attention wandered off to things that were happening, even if we were talking (like a loud car passing by-- can't miss those), and that pissed her off. (mistake? how to work on it?)

At the shore, a friend called and I figured why not answer, the convo was less than two minutes, but she seemed visibly bothered-- although she has previously done the same (mistake? should I have focused on just her?)

At the shore, she mentioned how she doesn't see how she and her kid fit into my life given my drive, goals, and ambitions, and I let her know that "hey if we've been doing this for a month then I clearly see something in it", that made her shut up and think.

In the end, I mentioned the whole "spontaneous" thing and she said "I guess indecisive is spontaneous now", and I played it off without breaking my frame. We went home, I slept over, and this morning she mentioned how she couldn't sleep because she cared too much about whether I was comfortable, cold, and shit like that. So.... what the fuck? How do I handle this? Seems to have a lot of conflicting emotions. I'm used to just leading and the women follow-- but damn, she seems to have had enough of me leading... or was it because I didn't have a solid plan?

Thanks for reading, brothers. Looking forward to your feedback.

TLDR: 19-year-old me going on dates with 31 year old for the past month, looking for feedback and criticism on how I messed up last night and how to fix behavior as well as address the "loss of connection" comment in future dates.

Any questions about more specifics will be answered... just ask em'.