Can’t tell if he’s interested

I (19f) and a boy I like (20m) went to high school together. I knew that he had a crush on me during HS and I liked him as well, but we lost touch after we graduated two years ago (partly due to me not being a great texter) and some other factors including the pandemic happening, and going to different unis (still near one another).

Nearly two years since we have last spoken, I get a text message from him and we have been messaging regularly for the past few months. What confuses me are his intentions. He has kept the conversation going for months now without fail, but he hasn’t flirted much ever and has never really initiated a date between us besides hinting at showing me something of his one time which I responded well to. We have video chatted a couple of times which he initiated, but that’s all.

If this was anyone else, I would take the fact he reached out to me in the first place and kept the conversation going as a hint, but his personality makes it so that he will literally carry a conversation with anyone for months, so it’s not a great indicator of whether he likes me or not. It honestly makes me suspect that he’s just speaking to me because he’s bored or wants to be amused since he might know that I like him.

It’s honestly torture for me to keep in contact with him this way without knowing if he has feelings for me, so I plan on either asking to hang out or straight up asking him about this, but I was wondering how I should go about that or if I should even bother. I would also like to hear perspectives on why he might be dragging the convo for this long without hinting at anything? Thanks