Why are you talking to him at all about dating? Quit allowing him to friend zone you! He's looking for your replacement, why discuss it with him?
You specifically said "I did manage to make progress and get him to say he misses me"..... That's progress? I know we discussed goal setting before. Is that your goal? For him to be your buddy?
34, xw33 M-10, T-18 2D (8 and 5) Ilybinilwy-1/16 EA/PA- 7/15-present (with my former best friend) Trial apartment-2/16 (also when she considers us separated) W moved out-8/16 W Filed 11/21/16 D final 1/30/17