The flow of this chapter makes it agonizingly painful to read.
They're both terrible at communicating their actual feelings and the circumstances of their relationship is actually kinda complicated with his Mom's involvement so I don't really fault either for that. The Mom's pretty passive aggressive and asserts a lot of soft power that I'm sure has determined how he's made and maintained relations until now. Something a little more has to change before I can see them choosing to date long term (not sure I want them to given the circumstances and Mom's initial behavior). That doesn't make it any less awkward to read and I'm still just left wanting them to be a normal couple who happened to be introduced to each other through the mother and ended up hitting it off.
And then there's the ending which is just sad. How are you going to squirm away from a date invitation like that? A girl asks you out on her own accord and you think it's just to make fun of you over paintings? God your mom really did ruin you. At least use your still then girlfriend as an excuse. I really thought the "she's smart" was going to lead into him asking her where to take his GF out to eat. Instead he runs away like a frightened animal and it ends on that weird note of her asking the manager about him.
As always, the trope of socially unaware or otherwise "loner" characters having 2 to 3 girls throwing themselves at them despite acting like... well this is in of itself a headache.
first off, he didnt think the date was specifically to make fun of him. He thought a situation in which they go and his lack of knowledge would end with her making fun of him would occur. Its not the same.
Secondly, he isnt aware of his feelings so we cant fault him for being indecisive because he isnt being like that, he just doesnt realize he is starting to like her. And he's not even incompetent despite being socially awkward.
Thirdly, i dont know why you're surprised another girl would be interested in him. We're already seen how he is viewed by other people. He's considerate and thoughtful from Asano's perspective but he also has an intense look that makes people feel a bit scared as we are told from those younger men's perspective during that beach event. And from his old schoolmate, we know that he agrees with them on that but also believes that he's a good guy. So he might be awkward in how he is depicted to us as readers and from his own inner thoughts, but OTHER people dont see it. They see him as someone who may be a bit brooding, a bit scary, but ultimately with good character. With that haircut he's also kinda handsome, at the very least he also knows how to dress presentably. Its just that the story is largely from his perspective so we only see him through his own eyes, which makes him seem worse than he looks to others. Its not at all weird a girl or two would be interested in him.
He's also not so afraid of interacting with people that he wont meddle in certain affairs, like how he went to find out more about Asano's old friend and took an opportunity to try and get them to be friends again. He went out of his way to do that not specifically because he is in love with Asano but because he wanted her to at least come out of the relationship a bit happier. Maybe he also feels indebted to her, or guilty over what his mom did, or because he liked her enough to have that kind of good intention, but regardless thats what he wanted to do for her. A truly socially inept person wouldn't do any of that. The glamping, the beach, they wouldnt be anywhere near it. He was right, he's a loner. Not some shut-in who cant talk to people or go outside.
That mom really did a number on him. My verdict? MC is not one to actively seek friends or change but wont just absolutely run away from them either like other MCs with that setting would. He can even be quite considerate of people, even enough to go out of his way for them in certain circumstances. Its just that his lack of self-worth makes him think of himself as a burden or something when no one else does.