How to know him better without going too far
I like this guy, and I think he likes me, but he is a senior figure in my profession, and potentially a good mentor: I don't want to screw up my work chances by being too forward and sociable, but at the same time I don't want to be so cool and professional he doesn't see I'm interested.
I don't think either of us are the types to be too concerned about a workplace-romance. My question is more about how to negotiate getting to know him better without embarrassment or overstepping the mark!
For instance, I find I contact him to ask his advice quite a lot, as a "safe" excuse to send a friendly email, but fear this might eventually (already...?) make me come across as only getting in touch with him when I want something...
We're both freelancers, so I don't bump into him out and about much, we only really meet if we plan to - at the moment only at his inception. It might seem pushy / inappropriate of me to ask him out socially. At the same time, I can't see the right alternative. I'd be so grateful for your thoughts.
By now, he must start having a feeling that you are interested or that you could be a potential date. You both look mature so my feeling is that you can be quite open about your desires.
Invite him to a social event a friend of yours is throwing, or send him a card with an invitation for a drink or something like that.
If he goes with it, find a moment to tell him about what is happening. Describe your feeling as something interesting and strange which is going on in you. Ask him for advice about what to do with it: "what do you think? Don't you think it's funny?"
In these early stages, the main mistake to avoid is to be sentimental. Keep it light, open, fresh and fun. If he does not respond, quickly move to another subject, very lightly, and let it go.
If at any moment you sound claiming, clingy, attached, dependant or desperate or even too deeply in love, that's it, you lose him!
Stay on the fresh, light, fun and free side. Many guys would avoid any close contact if it sounds complicate in any way. Be fun to be with.