How Can You Tell If He's Flirting?

Dear 100footer:
I tend to be a somewhat shy/naive person when it comes to flirting. Socially I am fine and do well making friends but when it comes to flirting I feel like I am out of my league. I really do enjoy conversations with people but after a great conversation, I always go home alone.

The guy and I will usually hang out a couple more times and then we just fade out or I make a friend out of the deal. I am just bad...no HORRIBLE at picking up signals. I have friends ask me, "what happened with you and that guy you were with last night?"

I reply "we had a good time and then we went home." They always reply with something along the lines of, "You mean you both went home...alone...separate?"

They always point out things like body language and tell me how they knew the guy was flirting with me. On a side note I don't invite my friends out with me, but I don't live in a big city and when I go out with somebody I am bound to run into somebody I know considering most of the gay people hang out on one street here, luckily I have great friends that will come up and say hi but leave me and my date alone for the rest of the evening.

Even if I am at the mall with friends they always pointing out that some guy was checking me out, but they always end up getting numbers and I end up wondering how they know these guys are into them. Well, one time I did know that a guy was into me at the mall, because he followed me to three different stores but then I got a "you want some candy?" vibe and ran.

I never pick up on body language or flirting, honestly I rarely ever know a guy is flirting unless he says so, BLUNTLY! My friends say that a smile it flirting, but I smile and say hi to people all the time and I am just being friendly.

Online it tends to be worse. I really enjoy chatting but when I see a profile that really interests me one of two things happen: 1) I send a message and get a response, we go back and forth a couple times then I never know when the right time to ask the guy if he wants to go out. 2) I send a message, get a response and then I just don't know what to say next in order to keep the guy's attention.

 
I mean I know that this is online and most guys are looking for sex but I do want something more substantial. Problem is how do I get it? Not saying I don't hook up with men, but for some reason asking for sex is easier than asking for a date. Crazy I know, but that is for another day. Please help me I cant be the only person who is signal-reading challenged right?

 
Sincerely,
 
Walking With Blinders On

Dear Walking With Blinders On:

What we have here is a cut and dried case of fear. It's like you don't want to get on the field unless you are absolutely certain of what you should do when you should do it, and how you should do it.

I understand that you are suffering from "signal interference" in the sense that you are not processing flirting signals correctly. I get that. But you have a bigger problem: Your unwillingness to get in the game and make mistakes.

Yes, there are plenty of books and advice that will teach you how to flirt but none of them are going to be of any help if you are unwilling to put yourself out there. And by putting yourself out there I don't mean just going out to bars, parties, and social events, but to actually taking a chance and making a move.

The best advice I can give you is to "act as if." Whenever you go out, act as if the guy you're interested in, and talking to, is flirting with you. Simply assume it and act accordingly. If you've misread him then so what? You'll be friends. But if you don't misread him and he in fact is flirting with you then you have a real crack at his, well, crack.

I don't want to go into all that is involved with getting your flirt game on because that is a longer conversation best saved for  books. But here's a hint: Avoid conversational dead-ends.

I do have to say you can't make an omelet without cracking a few eggs. You keep holding up the eggs and wondering, dithering actually, what is in the egg, whether its protein goodness is meant for you, and whether or not there is something in there in the first place. Just crack it! If there's nothing in it move onto the next egg.

Once you start assuming that good-looking guys are flirting with you, in other words, "acting as if", it will all become clear to you.

And all your bellyaching about misread signals will go away. Your fear is allowing you to conceptualize the problem too much. The problem isn't so much your inability to interpret signals (I grant you that it IS a problem) but the paralysis that overwhelms you.

Now go, and crack a few eggs.