This can be a huge question if you like someone that just will not seem to take the hint. There are a few reasons why this may be. The first step if you have a friendly relationship is to try and see if you can figure out why. It could be that he was interested in you before you became friends. A lot of guys think once they hit friend status that they are not dateable. If this is why he is not asking you out it is easy to fix. The simplest way is to ask him if he wants to go see a movie or something. You do not need to label it as a date, you could even take him with you to look for Angel flats and houses for rent. While you are out make sure that you listen to him more and give him those subtle hints that you would on a date.

If you are not quite at friend status and just acquaintances it could be that you don’t have all of the facts. He could have a girlfriend or a wife that just has not come up in conversation. He could also have just not noticed that you were interested in him. Maybe your subtle flirting is subtler than you thought it was. The best step to take here is to make sure that you do get all of the facts. Try a mildly probing conversation about significant others. You can also ask a mutual friend if you have one they may know. He could also be very shy and just afraid to ask you out or unsure of himself. If all of your hinting and subtlety do fail you can always just ask him out. I know it can be scary the fear of rejection can be very powerful and stops a lot of people from asking someone else out, but it’s a bit like putting yourself in his shoes.