MLB ANSWER: Hi Angie – thanks for writing in. One motto of midlifebachelor.com is ALWAYS GO FOR IT … so that is my core advice for you. Since your friendship with this man is obviously important to you, then you probably want to tread carefully just in case he is not into you. Depending on your own personality, I suggest that you drop a hint or two, and then see how he responds.

The “drop a hint” approach might mean that you say something to him like, “I wonder what would happen if you and I ever hooked up?” … or maybe you’d give him an unexpected compliment like “You know – you are looking pretty hot today” … or basically say something that fits the situation, yet steps up the heat.  An alternative to saying something is physically doing something that steps it up – like giving him a peck right on the lips (assuming you don’t usually do that).

Once you’ve dropped the verbal or physical hint – pay very close attention to how he responds. If he says anything that in any way changes the subject or shuts the discussion down, then you’ll know he only wants to be friends … and you should definitely be prepared for that. Recognize, however, that he also could respond with something unexpected and nice. You mentioned that you make 3X to 4X what this man makes – and frankly that makes some men uncomfortable … so also consider that if he rejects you, it might not have anything to do with physical or mental attraction, it could also be that he is intimidated by you financially. The converse of that is – your money might make him want to be your houseboy. ha ha

All joking aside – what I’m really suggesting is that you take whatever steps you are comfortable with to GO FOR IT … and be prepared for whatever the reaction brings. Don’t overbear – else you might lose the friendship. Good luck – let me know what happens!