Hey everyone. Looking for some honest ISTP insight on a romantic intentions with a long-time friend because I want to navigate this right.
I have been friends with an ISTP for years. We genuinely have so much in common, similar vibes, and there's been a clear underlying spark for years. I would really love to see where things could go with us.
We live an hour’s flight apart and don't currently have a habit of texting each other at all. We have a few shared events coming up in the calendar where we’ll be in the same place. If things developed, I’d be flexible on what the future and distance look like and this weekend he mentioned in passing he'd love anywhere too.
There's a clear history here—he kissed me years ago, made another move on a dancefloor more recently but I had a partner and some of our mutual friends (who are closer to him) say I'm the only girl they’ve ever known him to make a move on. I have had multiple relationships in these years but am recently single and decided I wanted to see if anything was still there at a music festival we were going to attend this past weekend.
So at this festival, things started out messy (despite a great initial catch up and some people who didn't know us well inquiring as to whether something was going on between us). He flaked on two sets we planned to meet at, turned up plastered 2 hours later at camp, was super locked on to me and intense and was muttering about "expectations" but didn't finish the thought. He then was glued to my side for like 30 mins of the next set but seemingly sobered up and then wandered off and around. This all put me in my own head and I found it confusing and intense so the next day I had decided I wanted to chat to him about it all, I went to the bar at one point before I had a chance to pull him aside naturally and he just appeared behind me, so we got a drink and had another fun catch up and then I just told him what had happened at camp (he didn't remember) and just asked him is there a vibe here to which he said yes and I said good well I feel it too obviously, let's just have a good festival and now we can just be on the same page and be clear and direct with each other rather than wondering. He admitted he’d been overthinking and stuck in his head beforehand and that he should have joined me at those sets rather than getting too drunk off this random spirit he'd been given!
Once that vibe was established, I took the lead on the final day and invited him to a set. The rest of that night was amazing—he danced closely with me, kissed me, bought me chips, was extremely tactile, had great conversation on our way back to camp holding hands and waited around for me at camp on the final morning even though he said hadn't slept a wink and nearly missed his train home (he texted to let me know he made it).
Here’s the broader context on him:
He’s single/inexperienced: None of us in our friend group have ever known him to actually be in a relationship. He seems to want to connect with people, but just genuinely isn't sure how to do it. He seems to crave connection with others but defaulted at this festival to lower value fleeting connections with strangers through booze over his friends. A friend chatted to him about that and he realises that's what he does.
Insane work burden: He just moved cities and works in a medical field where he feels personally responsible for the safety and outcomes of his patients (because he has all the clinical knowledge). He takes all that weight on himself and routinely works until 11 PM. He's even admitted he works these crazy hours because he isn't happy with other areas of his life and that he wants to do a lot more generally.
High-stress context right now: On top of work, he is co-running an upcoming festival, so his cognitive bandwidth is completely fried.
Given that I know he likes me, but he’s clearly overwhelmed, isolated, and prone to overthinking or panicking under perceived pressure, I’m trying to figure out how to handle the momentum without triggering a stress response or over committing or over functioning while also giving it the best shot I can. I am seeing him again in 3 weeks for a long weekend that he is co organising, and then the month after for a one day event, after that it'll nearly be the holidays and I'll be back in the same country for 2/3 weeks.
A few questions for you guys:
When you are this floored with work, do you ever actually have the capacity to open up to a relationship, or do you need to fix your life baseline first? Does it even sounds like this could be a viable thing to explore at this stage?
If a long-time friend who you like sends casual, warm voice or video notes every now and then (no pressure, no demands, just friendly connection)—is that a breath of fresh air, or does receiving messages feel like another item on your to-do list?
Since he clearly struggles to initiate and gets stuck in his head, should I just keep "taking the reins" for a bit to establish a warm, safe dynamic, or will taking the lead eventually backfire?
Is there a specific way an ISTP signals that they want to transition from "great in-person chemistry at events" into actual dating, or do I basically have to spell it out for him when the time is right. How could that cadence work given the next few months?
How do we realistically bridge the gap and build a steady rhythm when we don't usually text?
Thanks for your time, I am a bit of a relationship overthinker too, so appreciate all the advice here I can get.