Would YOU enjoy a relationship like this?

[Cumulum]

1. Neither of you plan dates, as in a scheduled out day of specific activities before the day of the guy picking the girl up. You talk about possibilities in text, but...
2. Activities for the day are only decided the instant she gets in his car, and after every activity until day's end. He asks "What do you want to do?", and if she parrots the same question in response, he says "I don't know, what do you want to do?" This can loop for a moment until she's the one who picks, every single time.
3. They may spend hours wandering in different shopping areas without a real goal in mind, just commenting about whatever is in front of them. He buys her everything at stores and restaurants.
4. Often, if he isn't already looking right at her face, or hasn't specifically asked her what to do next, if she tries to say something on her own to him a few times, he sometimes says nothing, at which point she drops her comment or question and they'll keep going.
5. Sometimes he'll walk right up to an activity and start interacting with it without turning his back to her, even if she tries saying something (see above). She'll end up quietly waiting for him to finish.
6. At least once, she can find her attention is suddenly taken by something even minor, and when she turns around mid-sentence to comment about it he's already meters away so she quietly runs up.
7. She often has to be the one to suggest one of the activities around them when they're out of the car, but sometimes she'll find once she's spontaneously suggested something he'll give a reason it's complicated, or they should do it later, and after back and forth where she tries to ask why because she doesn't understand, she'll often eventually agree to not. If he asks if they can do it later in the day, often they'll leave without doing it as all, and neither of them bring it up.
8. When he DOES suggest activities days in advance, it's a fair or going to a different city where they can pick almost at random after wandering around.  When he suggests while out in his car like usual (after she's already picked at least the very first one of the day), it will always be either scrolling on social media on one of their phones, or joyriding in his car in town aimlessly, either of which they can do for over an hour.
9. She's asked why he likes her, and he's said "You're nice, and pretty." When pressed he's elaborated "You've shown me compassion I've never felt from anyone before." And has at least once that "Talking to you feels like talking to an extension of myself."
10. He always waits for her to volunteer information about herself because he's already happy with everything he knows about her.
11. Whenever she vents about her emotions in paragraphs of text, he reassures her with comfort and how everyone who hurt her was wrong.
12. He promises to make sure she "never has to work again" so she can do art, how he "thinks of her all the time", how he loves her a lot, etc.
13. When he talks about his family, friends, or whatever he's heard about recently, he will talk and not mind if she never says anything substantial in response because he trusts she's listening.
14. When she asks "Does it bother you that I can't remember most of our conversations?" He says "no." He enjoys the feeling of them in tye moment.
15. He works a warehouse job on his feet all day, causing him brain fog, but feels refreshed by sexual thoughts about her.
16. She may lift clothing or guide his hand to a part, but in silence, he will sit there and breathe hard, or smile and say "I don't know what to do" and be told by her "I'm not expecting you to."
17. He can initiate jokes about sex, joking about "getting freaky in a hotel" bc they pass one only to backpedal with playful disgust about how gross they are. Or suddenly saying they should "do it in the butt" if the bans go through. If she asks how he feels about things, like "Do you want our first time to be scheduled or spontaneous?" He says "I'm not sure" and it's not elaborated on. Even if she asks something like "Do you want to go into a sex shop sometime?" And he agrees, they never set a date or bring it up again. This is the state of affairs even a year into the relationship, without ever having sex.
18. When they get the opportunity to physically sleep next to each other without having sex prior, he finds he can play with her breasts under her clothes without them ever having discussed this scenario prior, nor saying a single word to each other during. When she's the one to first give actual words to what happened, texting "Did you enjoy my body?" After being driven home, he can say he feels bad because he didn't ask, she'll say "It's okay." And the next opportunity to sleep next to each other and no other words about it, he feels okay to touch her chest the same way again.

[Gebidozo]

Most of these are just small trivial issues that mean very little, if anything at all.

Points 16-17-18 are the ones that require attention. One year into the relationship without trying to initiate sex is very strange. There could be multiple reasons for that. Are you both very young (under 18, possibly)?

[Cumulum]

No. We were in our 20s when this relationship occured. I just keep turning it in my head because I keep wondering how I keep thinking of both the little and big things, because I keep trying to convince myself they're all connected by the same general behavioral principle.

[Gebidozo]

5 hours ago, Cumulum said:

No. We were in our 20s when this relationship occured. I just keep turning it in my head because I keep wondering how I keep thinking of both the little and big things, because I keep trying to convince myself they're all connected by the same general behavioral principle.

I don’t see any connection, I also don’t see why those little things are so important. The only concerning issue, in my opinion, is him not trying to initiate sex within a year. Frankly, I can’t imagine a 20+ year old man having a girlfriend for one year and not trying to have sex with her. Maybe he has extremely low libido or is asexual. 

[ExpatInItaly]

He's not that into her, or perhaps not that into women in general. 

[smackie9]

This all looks like inexperience, and absolutely no imagination/excitement. This is all so boring. I wouldn't last 3 weeks if this was the way things were going.... No flame, totally lame.