Per my sheer opinion I never find it wise to mix professional lifestyle with personal lifestyle, it worked for my mother but she worked with the man for 7 years before dating. Since the only side we have is yours, I personally if I were in your shoes wouldn't really like the whole creepy flirting, with someone older than "us" they tend to usually be blunt and not subtle, so someone that is advanced at manipulation is what this sounds like and it comes off as viewing one as "frail" but not serious. I wouldn't stress it too much, but be cautious and wise, by wise I mean think logically and sound if possible, not with your emotions, when feelings are involved, it's never stable. Whatever we all say it's all opinionated, and if it's not what you want to hear, you're not going to listen. That's human nature, trust me. If so many people think something is amiss something does come off, I wouldn't rush into anything and would get to the know this person and why they approach you the way they do first. If he has your number he can call you, or even text you, be frank, and honest. Tell him you're not looking for games, it's best to be upfront with men because they don't know what you're thinking and you don't know what they are thinking. His vagueness seems wavering as if he's unsure but to base it off your feelings. Don't do what you feel is right, do what you know is right. Do NOT be swindled by someone just because they give you attention, that's a leading cause for swift mistakes. Good luck!