How should I tell my soon to be former manager that I like him?

How should I tell my soon to be former manager that I like him?

I (26f) like my soon to be former manager (27m). We’ve worked together for a year and a half, a few months as peers but mostly with him as my manager. I’ve like him for a while, but never pursued it. However, I’ll be starting a new job at a new company later this month.

I’m trying to figure out if he’s interested in me and if/how I should let him know that I like him. We’ve been very friendly, talking a lot during work hours about non-work things (e.g. family, college/past, random things that come up). We’ll just message for an hour at the end of the day on many days. We were working on a big project together and our meetings were always fun and a bit longer than strictly necessary. We talk occasionally outside work hours. During work, he initiates conversations as often as I do. After work, I reach out more than he does.

I’m confused by how much he talks during work vs how little he talks after work. I think some of it is because he feels the need to separate himself as the manager. He’s mentioned not wanting to send out e-cards to sign, suggest after work events like happy hours because he doesn’t want it to feel mandatory since it’s coming from the manager, or even attend some happy hour events and make people feel weird. I can’t tell if he said that to subtly remind me that in the work hierarchy that we’re not equal or it’s simply his self-professed introversion in action. Other times it almost feels like an afterthought as to how he thinks he should behave. He was driving us to a work event and he asked me about religion and then went oh wait maybe I shouldn’t ask you that because it’s one of those topics you’re supposed to avoid at work lol.

Segueing from that, I’ve tried inviting him to some events I’m doing with my non work friends. He said he was down for a haunted house thing we had planned, but backed out after his dad unexpectedly went to the hospital (understandable and his dad is fine now!) That was when I was still actively working there. Since accepting the new position, I invited him to go with us to see Christmas lights and stuff. He said it sounds fun and to let him know when and where we chose. The words were good, but the tone sounded unenthusiastic at least over text. Well when I let him know the details and mentioned he could get a discount on tickets from some site, all he said was that’s a great deal and he’s never used that site…nothing about whether he’s actually interested or not.

So I am left wondering if he just talked to me because we worked together and it’ll stop now that I’m leaving. Or if he’s interested and has a contradictory way of showing it. Does he knew that I like him or is he oblivious?

Also, I’m contemplating telling him directly that I like him since the indirect method of asking him to do stuff doesn’t seem to be working. No harm since I’m leaving right? Except to my pride if he goes omg ew no lol. Should I try to do it in person if he makes good on his claim to coordinate a farewell gathering for me? Or do it over message? It’s been on my mind nonstop.