I have a situationship with this adorable guy who happens to be extremely insecure and I don’t know how to’ unblock this relationship, any help?

[Anonymous]

He is an ex coworker i worked with last year, in February we met each other again and sometimes (not often) started chatting, it was obvious that he likes me, after a couple of months he started flirting when we were chatting, in April we went out together (we never discussed this attraction or the nature of our relationship, but it really felt like a date, he was romantic, flirty and kind; we didn’t kiss tho, just hold hands and hugged a little) by the way we had a good time and he was really kind, in this occasion he opened up quite a bit and told me he is feeling insecure and really down these days, he also talked about how him being neurodivergent in this moment makes everything harder cause he’s not even able anymore to take care of himself (I don't know what neurodivergence in specific but it feels like some sort of ADHD or something correlated to anxiety or depression) he said that sometimes this happens to him and he knows that he’s gonna come out of it, but it takes time and it can be frustrating.

He also made me take in consideration the fact that he thinks REALLY high of me and maybe even kind of idealised me, meanwhile he, right now, thinks kinda low of himself.

After we went out he wrote to me that he had a good time and we chatted a little.

After that we sometimes chatted but only after i texted first (i often texted first with this person, but he was always the one putting more emotions and flirting, i tend to be cold and take my time to open up), also, sometimes he just disappears for days or even weeks, he knows that and when i contact him again he says that he’s sorry but he’s still stuck in this bad moment.

Now it’s been since the last week of April that we’re not talking, i know for a fact that he’s still struggling in this bad mindset and there is no other girl, so I’m now here wondering… what should i do?

Should i contact him again or wait for him to contact me?

Updates

1 y

Important: we live in different cities, around an hour drive from each other

[Summeroflove]

Build trust with one another and have honest supportive conversations

[Asker]

So do you think i should talk to him?

[Summeroflove]

Absolutely

[SueShe]

It will be difficult to unblock that situation without medical help. This guy needs to want to have himself helped by specialists. What you can do though is to try to gather as much information as possible about his likes and dislikes and next time, gear the conversation towards a topic you know he likes. That should help making him more comfortable and actually even seeking the conversation with you.

He may even want to initiate the contact, knowing that you have shown interest in what he likes.

As for now, just send him a small "hi and miss chatting with you" message. Nothing big or long but just something to make him feel that someone cares for him.

[Asker]

Another commenter commented saying that this guy is probably not interested, do you think he is? Or is still a good idea to try to reach out?
The last time i heard from him (like almost a month after the “date”) he was still flirting but also really sad. I’m kinda confused right now

[SueShe]

Well, if he lives so far, you can try to contact him. I don't think you are losing anything by contacting him. It is not as if he wants to come to your place right away.

However, you have to be cautious too. Don't go headless and analyze everything he says and does. It could be that he found someone in you that is unique because most other women would tend to take their distances. He may hang onto you because you showed that you cared.

Let your 6th. sense be your guide. Better think twice before doing anything rather than to jump on the first opportunity. Good luck.

[strateguy632]

He waited a week, showed he is not interested. Tell him it is over.

[Asker]

But when i heard from him the last copule of times he still flirted (even tho i didn’t) and he was still in a bad mindset, do you think that he’s just not interested or is there something else going on?