No one except for my closest friend knows I'm gay. This really cute guy keeps texting me, and I have no idea what to do. I had a crush on him in middle school, and we were close acquaintances (not exactly friends) all three years. When high school started, he went to one school, and I went to another. I didn't hear from him until just recently. Out of the blue, he texts me and starts to flirt (well, what I perceive as flirting) with me. He mentioned he had a dream of me. Harmlessly, I flirted with him back making it out as a joke because I'm not out. This kid everyone thinks is gay, but had a girlfriend for 4 years until they just recently broke up. I have no idea if he is actually into me or is just playing with me. I can't exactly ask him flat out why he is messaging me because that would be rude. I can't say I still have a crush on him, but I do feel something for him. Has this ever happened to any of you? What should I do? Thanks in advance!
If he had no particular reason to contact you after so long, then it sounds he likes you. It's not really hurting you to keep on contacting him. Maybe you could even hang out with him for a movie or something similar. Just a few minutes of direct contact can tell you a lot by his nonverbal communication if he's into you. If you think he is trustworthy, you could come out to him. That would at least even the tables since he'll know that you are open to being more than friends.
The problem is that I've never hung out with him before. I've also never been the person to take the risk and "ask them out" even in the friendship case. I don't want to come off like I'm coming on to him (at least not yet) and risk him freaking out a bit. Like I said, I'm not even sure he's gay. Should I just wait and see where this goes? Or do you guys think I should just ask him?
It sounds like you're not really sure where you want this to go so there's no need for you to make the next move. At the same time, there's no harm in talking to the guy and you did like him a bit at one point so just keep talking and see what happens.
Go grab dinner, see a movie, go bowling, go to a sporting event, play video games, or something. If nothing else you get to hang out as friends.
Don't wait and see because he might move on, and you won't get closer even just as a friend. I know because being in the closet, I often had fantasies that some guy would just magically realize I was gay and ask me out, which never happened. I know it will seem out of character for you, but it really isn't hard to ask. To make things a little easier, try to say you were planning to go alone but was wondering if he wanted to come along. Or, ask him if he has any plans on the weekend. Choose an activity that both of you would be interested in.
Yeah, you guys are probably right. Next time we talk, I'll invite him out to do something. We'll just have to see how that goes... Thanks everyone!