Anonymous Caller Trickey Scenario Normally I would not need to ask how to tell someone out, but here I am. But, wierd situations call for different answers... You see, I'm bisexual, and I'm attracted to one of my friends in pretty much everyway. Except I have no idea if he's straight, bi or gay. He's never dated, and he doesn't really talk about any of those kinds of topics at all. What can I do? :/ Alucard Tepis A tricky situation, indeed.... Well, first of all, is he aware that you are bisexual? It seems obvious that he hasn't discussed it, but have you? That could lead to a lot of misunderstanding or his reticence at talking about it. If you concerned about "freaking him out" you are going to have to learn whether or not he would even be receptive to the concept of your being interested in him. Planting a big kiss on them as a first overture is not the best idea, but I think that is true in most cases. Do you hang out with this person socially? It would be useful to see him interact with other people. Does he ever seem interested in other boys or girls? Maybe you could talk to him about movies or music. Does he have a particular favorite actor or singer? Possibly talking about that, and what makes him like a particular celebrity could illuminate his preferences. Generally, and towards you, as the conversation gets engaging. Have you ever been into his home? It might be informative to see him "in his element." A person's room says a lot about their personality. How they keep it, how it is decorated, what they read, what they watch, what they listen to. Get to know him more closely (though probably not much more "intimately"), and you will likely figure out if he'd at least be receptive. If you get to know him better, you may even be able to slip, "Are you interested in anybody?" into the conversation. Here's where you are going to have to be at your most attentive, as body language and the tone of his voice may say more than his words. Potentially, it will be a big disappointment, but if he doesn't have someone else in mind, then you can at least get a better read on him. If you do find out he's at least pre-disposed toward your gender, and not interested in someone else, then I think the hardest part is behind you, and it sounds like you probably have a good idea about the rest.