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More than anything, guys love honesty. Playing hard to get is fine for the first few weeks, but if you think the feelings are mutual, playing around any longer is just going to hurt him and push him away. Wait a few weeks to see if you really do like him. Rushing into things is never a good idea, especially if you've already been friends for a while and are very close- rushing this would absolutely ruin your relationship. If you decide that you think you really want to date him, then by all means go ahead. Find a time when he's not with his friends, as putting him on the spot in front of them is just cruel. A brief meeting is all you really need at this point, as a very long timespan will make things awkward if the conversation goes sour. Walk up to him and gently say, 'Lately I've been having some feelings for you and I wanted to know if they're mutual. If they're not, that's fine, but I'd really like to know so that things don't become awkward between us.' Be very honest and forthcoming, but also gentle. Make it known that any answer he gives is acceptable and you're not putting him on the spot. Whatever he says, thank him for his honesty and ask if he'd like to talk about this in full later. Don't go through everything right then, as boys need some time to digest information and also need it in relatively small portions. (This is so they don't get confused or start double-guessing themselves.) Space each 'portion' of your talk so that there's a few days between each part, so you have time to digest the information and plan out what you're going to say. This will also allow for cool-off time if you had an argument or something. While this approach takes a bit and can be very frustrating, it works wonders in the end and will assure there are no bad feelings, whatever the outcome. Always be yourself, and never tell him things just to get him jealous; treat him with a great deal of gentleness and sympathy. For all boys act tough, they're human too, and they need to be treated like they have a heart. Good luck, and merry dating.