Thinking I should ask the guy out... should I?

So, this is a continuation of my original thread here: https://bit.ly/2vcBVf9

To summarize, I always felt my supervisor was a bit flirty... mostly in his body language and eye contact with me while I worked under him. He always seemed to be receptive to my, admittedly, subtle flirting back. I left and we kept in touch over email initially. After telling him I was planning a trip back (to see friends, not him), he dropped me his number and gave me a tour of his new office (busy boy).

I moved to another state 5 months ago, though we still work for the same company. All my coworkers heard about my plan to move. He acted a bit off around me, actually for the first time slightly aggressive, though not in a mean way more like treating me like a normal guy. When I told him I had something to say, he said something along the lines of "he was waiting for me to tell him." After this, he went back to being normal and sweet. Close to the end, I was sitting around and he leaned over me to get something off my desk. Like, his abdomen touched my arm. I was kind of thinking "wtf was that intentional?", when he did it again but slower this time. At this point, I got a little excited down under and had to excuse myself (asking for his permission ofc). I came back, and then he said "I'm dying, I need the bathroom," and scurried off telling me to watch the office. So I'm not sure if he was feeling the same way... or what... but the leaning thing tripped me out.

Last day of work, I asked him to show me how to do something while he was getting off. He ended up sticking around for 45 minutes teaching me something I... already knew very well (haha). During this, I inched my foot closer to his and tapped it. He moved away an inch or so... but then moved his foot towards mine, and our knees were touching. We said our goodbyes, and he said that "we should keep in touch"...

So, I moved to another state. Transferred within the company. I minded my own business for a few months, and then reached out to him over email (never got his number). I said that I missed working with him. And he said so as well. We shared some life stuff and changes in our workplaces,that was that. I had kinda dismissed him as just being a flirty guy and left it at that.

Buuut about 1 month ago, I planned a visit to my home state. He had shared he was promoted within the company. My trip was actually (not sarcastic) unrelated to this--went to hang out with some old friends. So I reached out and told him I'd be in his city and wanted to check out his new office. He said sure, and then left his number in an email telling me to reach out when I'm there. He did say that he would be off the next day... but I (maybe stupidly) replied that I had all of my time booked. Anyways, we met at his office. He showed me around and we talked a bit. He then asked if I'd be back in the city. I told him yeah, I plan to be back.

Since then, we've been texting each other. I didn't think too much of it, since we mostly talked about work stuff. I asked him if I ever stressed him out, while working under him (I was completely new). He left a pretty long response that basically said "nope, not at all" and mentioned some specific time he was impressed with my ability to learn and change something work-related. But somehow we started talking about the weather (snowstorm). I (probably failed) tried to flirt over text and said "I can't handle anything over six inches" (haha). I think context-wise, this probably flew over his head. He's also shared that he plans on visiting my state in a few months. We also talked about some of our hobbies... and talked about places we like to visit. I also told him I want to move back, if possible. But also said... on the crazy side... I want to live abroad. So we talked about where we'd each want to go as a "dream" country. Sometimes he'd also share things at work. One time, jokingly blaming me for being "bad luck" as we had just talked about crazy things happening at our workplaces... and something happened to him.

So, surprisingly... my flirty, hunky, supervisor has actually kept in touch with me. I really keep in touch with this guy more than anybody else back home, and arguably in my new place. It's been basically a year since we met and I wanted to know the guy and be around him instantly. But, at this point, even a few states away from the guy my feelings haven't really gone away. Actually, since the whole texting thing started I feel like they've gotten stronger. In a way, it's like... proof that he wasn't just messing around at work and that he's actually interested. And maybe me literally checking out his office indicated to him that I'm also actually interested.

Through it all, neither of us have straight up said "I like you." But we have both said things like "I miss having you around" or "I miss working with you." He's been very supportive of my whole move out here and gives me advice on things. I hold the guy pretty near and dear to my heart which is crazy for me to say. I'm not really sure what I mean to him, but he does mean a lot to me. I have thanked him for kinda setting me on a good trajectory career wise, and also allowing me to explore other career options while under his wing and discovering where I feel I belong. He said he was glad to be a part of allowing me to follow my dreams.

In any case, I have a trip planned back and realllly want to ask him out to coffee or lunch. Good idea?

Not even sure if I'm looking for replies. I just needed to type this out.

 

Interestingly (or maybe not) while talking about management at our offices he said "if you're like me, then you appreciate people being straight up." Was he trying to tell me something?

 

Here's an update.

I ended up just following my intuition. I told him I'm planning on flying into town to attend a concert (somewhat a lie, as I was interested in going but now am not...). I asked if he'd like to meet up outside of work to catch up, and he said definitely! So we have planned a hiking trip to a place an hour away from town. He got his days off, and I told him "so I don't have a car... I guess I'm not so subtly asking if you can also give me a ride..."

Anyways, my trip is 4 days away now and I'm desperately trying to manage my excitement and nervousness. We've gotten a little less chatty except for confirming the day we're hanging out. And he seems to be a little more funny over text, kinda like how he was in person. So that's been a nice reminder about how his humour... really just him as a person... can bring a smile to my face.

Also told him I'm looking at moving back and have interviews for jobs (my move was a temporary decision, needed space and time to progress my career). He said he hopes I get it.

I'm very excited, but nervous that he's just being a friend. For what it's worth, all my old bros know I'm gonna be in town, and we haven't made any plans lol. Just gonna do whatever... I dunno.

I have so much love and appreciation for this guy, he's done a lot for me. Being around him and having his support has meant a lot for my personal and professional life. And I don't wanna lose a good, meaningful, friendship with him. But I feel really strong for him. I hope there's more. Honestly my feelings now are stronger than when we still worked together--I did not think this would happen. I get excited just at the thought of him, or seeing a text from him. And then that turns into nervousness that it's just me.

 

I should add that I told him I'm no longer going to the concert too! So he might suspect this was a bit of a fabrication. I honestly planned this trip to test the waters, and bought these tix after he agreed to meet up.

Say what you will, but my mindset is that it he bails... I do still need a vacation, and it being my hometown I have a solid group of friends to chill with.

That being said, god I miss him. Whatever the outcome, I'm happy to get closer to an answer.