Guy Probs.

I will start off by recommending strongly against getting a friend to ask him on your behalf. They can’t be expressive in the right way and the most effective person in terms of asking any person to be your boyfriend is you.

What you need to do before asking someone out is drop a few hints (preferrably ones which have subtlety to them). You don’t want to jump to any conclusions just because he seems to interact comfortably with you. In this case it is likely that he sees something in you, but I am not the one here who is fit to reach such a conclusion. Interact with him perhaps a little bit more than you do or on a more personal level.

Try to organise lunch with him one day (on a weekend) and try maybe texting him every now and then and see what happens. In other words, imply to him that you like him without making it too obvious. If he continues to give signs to you that suggest he feels the same way then you should ask him. What I am saying here is that you have to be a little bit more ‘sure’ (for the sake of your confidence) than you are at current.

Be yourself and that is the best way to go about things (don’t be conservative/ shy). Instead of just letting him ask things about you, ask him to tell you some things about himself. Try to talk/ interact with him more (and more closely wherever possible) and observe whether or not his comfort level changes. Hopefully the signs he gives you will be positive. If you know this person well, use that knowledge to help you interpret the situation and the signs he gives you. Good luck with it :)!