Should i ask my friend if he still has feelings for me

Ive been on and off again with a friend for years. We've never done anything or so (except he kissed me once).
He lives 3 hours away and none of us are good at taking intiative to travel due to anxiety so its been hard for me to know how I feel.

Last time I went to visit him was in January 2020 and he treated me like a friend even called me his best friend... I assumed he was no longer into me so when I got back home, I started texting an ex. Then on valentines day he texted me he wanted to plan a romantic date for us. It annoyed me because he'd not shown any romantic interest recently. A few weeks later he asked me if I wanted a nude and when I laughed at that question of his he stopped texting me out of embarrassement. When I texted him again 2 months later he told me hes in a long distance relationship with some chick he met on Discord. Two years ago.
Hes started texting me more and wanting to come see me, then he told me hes sad because his internet gf told him now that their relationship isnt real and that they are friends... I just stopped dating somebody myself whom "friendzoned" me by saying he feels we are just friends lol like literally the same week too (my friend doesnt know this)... I'm not very upset tho because I wasnt in love.
This has happened before. The timing is always the same for us. I am feeling I should be with him and feel more ready in my life now.
Is it too soon to ask him if he still likes me or to ask him if hes truly in love with Discord-chick (even though he never met her). She only 'dumped' him last week. I could ask him because we are close friends so maybe it would be normal to check so its not confusing. Should I do this yes or no or wait until after we meet again which will be in mid December if all goes according to plan but for me it would help to know first because im very socially anxious.