There's a guy that I've worked with on and off for two years now. We're pretty good buds, and usually work well together. We have a ton in common, and I feel like we generally have a good time together when we hang out. A couple jokes, enough deep stuff, clear mutual respect, and plenty of awkwardness. It's very obvious that we care about each other. I have deep rooted trust issues, but I fully believe him to be a good guy with the right intentions. Overall though, he's generally sweet, complimentary, tells me I'm awesome and stuff like that, and is quick to help out. We joke around, he teases me in the best way, and makes me laugh my head off on purpose.
I also know him to definitely not be fake. He is honest, generally in the best way. I. e, still trying to be encouraging, but he isn't gonna lie if I make a comment about my hair or something. Here's the thing. He has clear boundaries in his mind. I. e., he is not comfortable hanging out outside of work. But I am the one who initiated that conversation, too. The way he worded it though, was "I just don't hang out with anyone from work. It's just not something I'm comfortable with right now." That's a fair boundary that I respect. I was trying to gage his response and basically said that I better see him after he leaves at the end of the summer. There were crickets. I was like "You're like nooope." And he pretty much said that he was just excited for his plans that weekend. That tells me he really wants nothing to do with me, but I'm fun to hang out with at work. He did tell me that he'd let me know when he does want to hang out, but I don't remember when. Which mega confuses me. He seems to think pretty highly of me, but I'm not a mind reader. So what the crap is going through his mind? It was a super awkward conversation. Our whole relationship is awkward though, but it's fun and deep and all the things.
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Have you discussed with him if he is already dating someone outside of work?
Everything you've said up there suggests to me he is enjoying working with you, but the reason he wants to keep work and pleasure separate is because of a relationship!
I could be wrong of course!
He definitely does not have a relationship. :)
Ok. You clearly know him better than any of us. Why do YOU think he is tentative about seeing you outside of work?
I only know that because we talked about it awhile ago. I honestly can't tell if it's me, or just a strict boundary that he's laid out for himself.
I personally am not someone who likes to pussyfoot around situations like the one you're in.
If it were me in your position, based only one what I've read... I would ask him,
"Do you subscribe to the notion, that dating someone from work could cause a bad atmosphere assuming it didn't work out?"
If he says yes, it's his policy. If no then it's you!
He playing his own selfish acts and sounds like you meting in it, not a smart idea.