Benny- Here's a question for you.
There's a woman who lives very far away from me. She's a friend from way back. She's a wonderful person and is apparently very good-looking, based on what other people say about her. (Sometimes, I find her attractive; sometimes, I don't- plus, it's hard to make a decision based on photos). We talk a lot- I texted her once saying that I was bored on Valentine's Day being around a bunch of couples (I have to admit that I wrote her first, wishing her a Happy Valentine's Day and such). She texted back saying that that wouldn't be if she were here. She usually makes very sweet comments when she calls. I'm not saying I don't like her like that; I just don't know. But she's visiting me soon!
Am I worrying over nothing? Am I being conceited? Am I leading her on? And how do I figure out my feelings for her, while, at the same time, toeing that line of a friend?
-Tom Cat on a Midnight Spree
Actually, I'm just going to call you Tom.
Anyway, Tom, thanks for being the first male to submit.
I'm going to start by answering your concluding questions directly.
-Am I worrying over nothing?
Yeah, pretty much.
-Am I being conceited?
Conceited? Not necessarily. Narcissistic? Maybe. I think that many of us sometimes have a tendency to blow situations out of proportion when somebody is interested in us... particularly those of us who have felt unpopular or "unfuckable" at one time or another.
We often have an almost-involuntary reflex of a voice that says, 'This girl is into me, so I better do this right or else I'll be a loser.'
Oftentimes, this reflex continues no matter how many situations we've been that in theory should serve as proof of our "fuckability."
We get this question in our heads: 'What am I supposed to do?' And that question often trumps another more important question: 'Do I want her?'
-Am I leading her on?
You don't appear to be leading her on based on your account. If you were to say, 'I can't wait to see you, I have a crush on you too,' that would be leading her on. If you were to have sex with her while still being this iffy about her, you would be leading her on.
Another tendency that many of us who suffer from the "Chronic Unfuckable Blues" have developed is to assume that other people are as lonely as we are at our worst.
Let me explain. When I was at my most shy and lonely, I very rarely acted on my feelings. It seemed like such a huge step even to banter with a girl in a way that would demonstrate my attraction. So when did I act on my feelings? Only once my interest had developed into a massive overpowering crush. Only when I'd been admiring her and thinking about her for months on end. I held it in and then let it all out in a massive explosion of emotion only after it had become far too intense to hold in.
A history of this type of introversion can obscure an important fact: many people don't operate like this at all.
Most people actually operate more like this:
'I'm kind of into this person. I'll let them know. OK, this person likes me. OK, let's see how it goes.'
'I'm kind of into this person. I'll let them know. Oh, they're not that into it. OK, good to know. Move along. Next!'
Here's what I'm getting at: You're probably not doing anything as powerful as "leading her on," with all the negative connotations that has because, seeing as she hasn't spent all that much face-to-face time with you, she's probably only very mildly into you.
-And how do I figure out my feelings for her, while, at the same time, toeing that line of a friend?
Hang out with her. Maybe make out with her. Don't have sex with her unless you decide you actually like her. In fact, don't even let her suck your dick unless you decide you actually like her. (I guess that stuff passes for casual among daredevil middle school girls, but, let's face it: most girls who aren't daredevil middle schoolers will only do it to a guy they really care about or a guy they desperately want to manipulate.)
My take on this girl is that she either A) is really intensely into you in a long-distance, idealized way or B) is kind of into you and doesn't have anything else going on, so she figures, hey, I'll sweet talk this faraway guy I'm going to see soon, and maybe it'll turn out cool.
If A is the case, then she could be bad news, and you should be cautious. If B is the case, then just take it as it comes.
Also, say to her what you said to me. At some point when you are hanging out with her, say, 'You're attractive, but I'm not sure if I really like you yet.'
I also want to call our attention to another thing you said in the message: 'She's a wonderful person and is apparently very good-looking, based on what other people say about her.'
What other people say about her should not matter. When you see her, stop asking yourself if she's hot or not. That voice will probably be there, but turn it off. Let the situation develop however it is going to develop. That voice that's questioning your attraction (or lack of attraction) to her will only distract you from what matters, which is the quality of the connection you have (or lack) with her.
In Improv comedy, one of the first things they teach you is to trust the other person to provoke "the funny" rather than attempting to constantly create "the funny." The idea is that comedy comes from truth and truth comes from genuine reactions. I'm not certain exactly how this relates to your situation, but I'm pretty sure it does.