How Do I Get A Shy Guy To Initiate The Conversations?
By approaching him! Be direct, be bold!
You can’t wait for everything to be handed to you on a silver platter, if you want it, you have to go and get it! Other people will suggest little ‘tricks’ and ‘games’ you can play to get him to approach you, which sounds exhausting, and so that his ego isn’t damaged, which is ridiculous. Why would you want to be with a man who’s self-confidence is so low that being approached by a woman and asked out would destroy it completely?
There’s an unfortunate attitude that is still pervasive in this day in age that women somehow have to wait for men to approach them, as if it is somehow emasculating for a man to be approached by a woman. Sadly, my older brother follows this school of thought, and has stated to me that if a woman was to ask him out or his girlfriend asked him to marry him, he would decline. That sounds terribly sad, that you would miss out on getting to know a potentially interesting person and that you would abandon your relationship with someone you love just because of some outdated societal ideal, that you are somehow less of a man for not completely 100% of the time being in control of your relationship.
So don’t sit and wait for men to approach you, you’ll miss out on meeting a lot of great people! Women can be the “chasers” just as much as men can!
This answer originally appeared on this Quora question on Shyness.