Is my staff member "flirting" or just being friendly.....

Your responses are that of a 'nice guy' - do you wear a fedora? If not send her a pic of you in a fedora
 
I'd do a check to see if she or her family are well known for no win no fee claims before proceeding :cry:
 
Happy to be wrong about this, but I feel you've made your thoughts pretty clear (in an appropriately coy fashion)

Even if you weren't her boss I'd be suggesting you take the hint. I feel you're right about the "not worrying tomorrow" part and yeah, I agree there's loads of potential she's trying to keep you sweet given your position of responsibility.

IMO you need to put the ball fully in her court on this. Chatting is not "signals" and guys are notoriously bad for inappropriately acting on misunderstood "signals" that are woman simply trying to cope with the hidden pressures they have in a workplace and level the playing field.

If it's a career you care about be super careful.

Edit: On second read she could honestly have a boyfriend - although I'm not saying she does :) All she's agreeing to is catching up with a friend and giving you every possible way out.
 
The thing that threw me is the "but you're not working tomorrow".

There's a difference between just popping out to Mcdonalds during work versus meeting outside of work, but her first reaction was the fact I'm not working.
Be confident. Maybe that was just a poor joke. I think that you need to take a little chance with these kind of things. Like I said, you'll know if she is keen or not pretty soon.

Be confident but don't lay it on too thick, if she comes up with an excuse not to come, just brush it off like it's not a problem/you don't really care and then move on.
 
IMO you need to put the ball fully in her court on this. Chatting is not "signals" and guys are notoriously bad for inappropriately acting on misunderstood "signals" that are woman simply trying to cope with the hidden pressures they have in a workplace and level the playing field.

I think that's nailed it. and I think I may be mistaking her friendliness (and fear of awkwardness at work) for something more.

Not even sure what to make of her most recent message with apology for the XX
 
Be confident. Maybe that was just a poor joke. I think that you need to take a little chance with these kind of things. Like I said, you'll know if she is keen or not pretty soon.

Be confident but don't lay it on too thick, if she comes up with an excuse not to come, just brush it off like it's not a problem/you don't really care and then move on.

What are your thoughts on the most recent message?
 
What are your thoughts on the most recent message?
Realise you didn't ask me but I've sent kisses to my male boss after texting back and forth with partners in the past. It can easily be exactly what she says as she'll likely have girl friends she taking to as well - if not a boyfriend :D
 
Realise you didn't ask me but I've sent kisses to my male boss after texting back and forth with partners in the past. It can easily be exactly what she says.

And it probably is.

I think I'm just over analysing and looking for something that might not be there.

Best thing now is to just ghost her and ignore her at work....
 
And it probably is.

I think I'm just over analysing and looking for something that might not be there.

Best thing now is to just ghost her and ignore her at work lol (the last part is obviously a joke)
There's also an option where you aren't a gigantic fedora wearing lame-o. Just be a normal civilised human and not think every kind women wants to be smashed when they are civilised.
 
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