Should I text my former boss again, or just leave it?

[NewHere92]

I could really use some advice and an outside perspective on this situation.

I used to work with a director who eventually left the company to start his own business.

We worked together for about a year, and during that time, he always seemed genuinely impressed by my skills. We successfully completed several projects together, and professionally, we made a really good team.

However, the last few months of working together were a bit strange. There was some flirting between us, but also tension and mutual accusations.

At one point, he hinted that he’d like to bring me into his new startup. But given how tense things had become between us, we never really discussed it further.

Fast forward a year. He found out that I’d left the company too, reached out to me, and suggested we meet for a coffee date.

This was in mid-September, just before I was leaving for vacation. I told him I’d be back in early October.

We tried to find a time to meet before my vacariob, but he was extremely busy with the official launch of his startup.

I was the last person to send a message, and he hasn’t replied since. It’s now the end of October.

The thing is, I genuinely want to see him. I’m interested in him as a person, and I’m also interested in his project.

I know he has a tendency to forget to reply to messages, not just to me but to other people as well.

Still, I feel embarrassed about reaching out again. I don’t want to seem like I’m chasing him or trying to force a meeting.

So my question is: Should I text him again, or should I take his silence as a sign that he’s not interested?

I’m honestly so confused. On one hand, I was the last one to text, so I feel like the ball is in his court. On the other hand, what if he’s actually waiting for me to take the initiative?

The problem is, I’m really bad at making the first move. I get embarrassed, I overthink everything, and the idea of reaching out again makes me feel like I’m chasing someone who might not even want to see me.

And I’ve been stuck in this exact dilemma for six weeks now.

[ExpatInItaly]

3 hours ago, NewHere92 said:

There was some flirting between us, but also tension and mutual accusations.

What sort of tension, and accusations of what nature? 

3 hours ago, NewHere92 said:

I was the last person to send a message, and he hasn’t replied since.

What did you say in your last message?

[NewHere92]

32 minutes ago, ExpatInItaly said:

What sort of tension, and accusations of what nature? 

It was all work-related. He was leaving the company and wasn’t wrapping things up properly, which ended up affecting my work. I got frustrated and sometimes lost my temper over it.

 

33 minutes ago, ExpatInItaly said:

What did you say in your last message?

Our last exchange was when we were trying to find a time to meet before my vacation, right around the launch of his startup.

He suggested 2–3 possible time slots, and I told him one of them worked for me. This was just two days before my flight.

He also added something along the lines of, “If none of those work, then in October. let me know ”

I replied that one of the suggested times actually worked for me, but otherwise, yes, we could do October.

And that was it. He never replied after that.

[Alpacalia]

The only real wrinkle is that you’ve got two things tangled together (the flirty history and the possible job), and you should decide which one you’re actually after before you text, because “coffee with a charming ex-colleague” and “coffee about joining a startup” are different meetings with different risks, especially given that the last months of working together included tension, mutual accusations, and flirting all at once. So lead with the professional angle, which is also the lower-stakes, easier one to send: “Hi [name], hope the launch went well! I’d still love to catch up and hear about the startup whenever things settle. Coffee in the next couple of weeks?” Short, warm, specific, no apology, no “sorry to bug you.”

[La.Primavera]

Based on what you have written, I'm seeing red flags professionally and personally.  I wonder if your hesitation in texting him is your intuition warning you that this is a bad idea.

[ExpatInItaly]

1 hour ago, La.Primavera said:

Based on what you have written, I'm seeing red flags professionally and personally.  I wonder if your hesitation in texting him is your intuition warning you that this is a bad idea.

I was thinking the same thing after having read OP's follow-up to my questions. 

This just doesn't like a wise move, OP. If you had work-related tension before to the point where you lost your temper, perhaps it's better to avoid trying to take this connection any further. It doesn't sound like you two really line up on a few different levels.