Yo I wanna hit him up but I'm scared

So there's this dude, super cutie, really chilled out and charismatic. We used to be in light contact on and off about a year and a half ago. we didn't speak after that school year much (because of classes, scheduling and such).

I distantly hang around this chilled out cutie( because of having the same friends) , and I'm pretty interested now. However. I don't know how to approach him to get to know him better (i mean we both skate and such but) and I feel like it would be weird if I just all the sudden slid into his dms after what, a full year or two? My ex agreed to hook me up (because he's a legend), but idk. Any advice on how to get back in contact with this guy?

Lmfao, advice is much appreciated!!💖💖💖