Reinitiating Interest after Months of No Contact

I met this guy at a work event series early last year. Throughout the few months we were working together we would hang out as a group and became closer. At this point I found him attractive, but wasn’t sure if any of it was reciprocated.

After the series ended, he initiated to hang out outside of work just the 2 of us. Over the course of the next 1.5 month we hang out 3 times (I initiated once) because both our schedules were extremely busy and it was harder to find free time. But when we did hang out it would be 4-5 hours long conversations and I could definitely feel my attraction grow and had a feeling it was mutual. If not I really don’t think he would want to hang out with me outside of work.

During one of these hangouts, he explicitly mentioned he was single too. I thought things were going great and eventually he would make a direct move and ask me out on a date. However, towards the end of last year I had travel plans for a few months and he also had travel plans and … things kinda just stopped. His texts had always been a bit dry so anytime we were texting I couldn’t tell if he was interested which made me overthink. And our last text convo was a bit dry and I also can take a little bit of blame for seeming closed off/ uninterested even though this wasn’t true. However, in person the conversations were always great.

I need advice: It has been 5 months since our last text. He has almost every quality I want in a partner I regret not shooting my shot during one of our hangouts and still sometimes wonder if things would be different if I did.

I’ve been busy the past few months with various things and know he has a pretty busy work/social calendar as well. Based on the vibe I get from him, he seems very respectful and I don’t think he would’ve made a direct move first to avoid making me uncomfortable. Also, since it’s been 5 months I’m not sure if he’s dating anyone or is even still interested in me. I also did randomly run into him on the street one evening a few weeks ago (we were across a few blocks so not talking distance) and we just waved at each other and kept going our separate direction. I wanted to see if he would text after but he didn’t.

I keep hearing things from my friends along the lines of “if he wanted to he would” , and I shouldn’t be chasing someone who clearly didn’t pursue me - which is making me hesitate. What’s the best way to reach out after months of no contact and not make it weird?

TLDR: Met this guy through work event- hung out a few times and had great conversations. Because of busy schedules/no explicit conversation that either was interested we haven’t seen or texted in 5 months. Wondering if I should drop it cause he’s not initiating or if I should reach out.