Im sort of stuck..idk long story ❗❗

I'm super shy, I'm always attracted to super shy guys too, or socially awkward because i feel like they might understand what it's like. But..theres this one guy I used to party with (by party, I mean sit around drink a few beers, talk about music bc we're both super into the oldies) I really liked him, and we hooked up a couple of times a few years ago. And of course i caught feelings..And he told me hed love it if I'd be his girl..it was kind of difficult because he was trying to get himself together, he had a good job and everything he just Lost his licence a few years before that for something he shouldn't have been doing. We werent able to hang out much unless his buddy would bring him by, and he did often at the beginning bc he thought wed hit it off.. so we texted. We texted for May be a few weeks, and then he couldn't come out to see me (I didnt have a car at the time either, money issues) and I understood that, but after a while, I would text him, and he just acted like he didnt have the time to reply. I tried calling him a few times, and he Never answered. After that, I just gave up bc why talk to a brick wall? I just felt like I was talking to myself..but since then, he texts me every once in a while, like over the past few years, always wishes me happy birthday and merry Christmas, how have you been texts..he calls me little lady. And I always thought that was cute, because I used to call him old man. We're both still single, he's moved out of his parents place and got his license back. He still texts me every once in a while, "so how have you been little lady?" But it's like idk..id really like it if we could get together and talk or hang out like we used to, maybe see where things go but not pushing the envelope.. but I'm so scared of being rejected like I felt I was a few years back. Idk if he just doesn't know how to approach me, or if he's just being a friend, checking up on me every once in a blue moon. Does this sound strange?? Idk any advice is welcome.