I'm a college freshman and there's this girl that I like. We've been friends for a couple years and we talk fairly often. Half the time when we talk, though, I leave the conversation feeling unsatisfied and annoyed at myself. Sometimes when I call her, I run out of things to say, and have long awkward silences, sometimes I start talking about my emotions and weaknesses and then feel like I'm being, or making myself look weak or wimpy. I have a bad habit of apologizing excessively for minor things. I feel like if I want to attract her I should try to flirt, be cheerful, and confident, but when I talk to her I'm usually uncertain, serious, and slow-speaking. I use far too much filler language ("like", "I guess", "I don't know", "yeah", etc.) Sometimes when I concentrate on avoiding these things I have better conversations, but most of the time I don't and end up ending the call feeling awkward and certain that she must find me unmanly-not a possible target of affection. Can I get some advice? 

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Great articles there! Read them and live them.

Don't be too hard on yourself, flirting with girls doesn't come naturally to the majority of people. It's something that must be learned through practice and making mistakes.

I found that just talking to people in general, striking up conversations with total strangers, helped me immensely. When I was younger, I would try to talk to at least one stranger a day, giving compliments, asking questions, and trying to charm them. Over time I noticed people would respond to me better.  I found little old ladies were the best for this because they often have led really interesting lives and have a lot of cool knowledge to share while being very approachable.

With regards to your intended target, show more than tell.  Talking is great but actions are better.  What I am getting at is ask her out. Then, when on the date focus on having fun and keeping it light hearted and warm. I know it can be really hard to make the first move but if you don't eventually another guy will and you will be left standing on the sidelines.  Get yourself into the game, if you want some ideas on how to do this hit back a reply.  Just keep it simple and make it clear that you are asking her out on a date, not as friends.

Hyrum, so there's a girl that talks to you regularly. You talk about your emotions, and she seems to enjoy it.

Maybe she's not looking for a smooth talking guy, who knows how to flirt. Maybe she likes you for who you are. I mean she keeps talking to you, right? Maybe instead of trying to smooth talk her, just tell her how you feel.

Ten minutes spent in silence with her hand barely touching yours will be electric.

Go for it, buddy.

Hyrum, most of what you mentioned is symptomatic of being self-conscious. Go back and read all your self-observations regarding your performance. Enough about you! What about HER? Your attention needs to be on HER, not on yourself and your performance. "Where attention goes, energy flows"--meaning that by obsessing over the flaws in your performance--you're actually feeding them!

Sometimes when I concentrate on avoiding these things I have better conversations but most of the time I don't

That's right; concentrating on what you are saying burns up a lot of your bandwidth and is hard to maintain, isn't it?

Instead of concentrating on what to say, or not say, you need to maintain the right mood and frame of mind. I don't know exactly what is right for you in that context, but it might be something like "friendly, curious, cheerful, affectionate". Maintaining your mood is more important than any specific thing you say or don't say; when you are in the right mood, you'll tend to say things that are congruent with your friendly, curious, cheerful mood, and it will sound a lot more articulate.

It's called the "access state principle". It means that it's easier to remember and talk about whatever is relevant to your mood. When you are angry, you tend to remember grievances related to incidents that made you angry in the past. When you are happy, your mind is more likely to wander to pleasant memories that bring a smile to your face.

When you are scared or nervous, you will find it difficult to say something clever, fascinating, or charming. Instead of trying to think of something appropriate to say, you need to take care of your own mood while you are with her (or anyone else), and the words will flow naturally.

Unfortunately, you have built up a habit of becoming nervous, that is triggered by her presence. You need to unlearn that habit and learn some new habits.

Here is some homework for you:

  1. Start a habit of thinking positive thoughts. Count your blessings. Think of things that go right in your life. Think of ways to turn around setbacks. This will improve your baseline mood, which will work wonders for your articulation and charm.
  2. Play a little game. It's called "what I like about you". Whenever you talk to someone, even and especially if it is someone you don't particularly like or admire, think of reasons to like that person, or at least feel compassion for that person. Practice on a lot of different people, including people you would not naturally be drawn to. For example, when a bum comes up to me to beg me for money, instead of shying away anymore, I may give him a few kind words and a friendly pat on the shoulder. The purpose is to build up your empathy. The more empathetic you are, the easier you will find it to relate to others in a satisfying way.
  3. Imagine that you have powerful empathetic--almost telepathic--abilities, you just don't know how to use them, but you're going to develop them by paying close attention to any emotions that are expressed, even fleeting microexpressions...set a strong intention to be able to read her mood and if possible her mind. Be genuinely curious what she is thinking and feeling. Try this with everybody. Maintain strong eye contact while doing it.

Some of my friends find this "intrusive". It's not, as long as it's done in a friendly, respectful, empathetic way.

You don't have to say all that much. Sometimes you're a better conversationalist if you shut up and listen, after asking thoughtful questions. Be curious (curious, but not intrusive!! Don't ask inappropriately personal questions! Public knowledge only please) about other people, their feelings, desires, dreams, interests. Most people respond well to an interest about themselves, and love to talk about themselves.

You should only be talking about 20% of the time anyway. If you ever see a man talking a lot to a woman in a bar, trying one clever thing to say after another, and all she has to say is "uh huh. Right. Sure....", she's not interested. The person trying too hard to win points by saying the right thing is demonstrating a desperation for approval. It's OK to have nothing to say sometimes, and just look at someone, and break into a friendly, approving smile. Stop feeling desperate to fill in those pauses, and relish them.

Great success to you in matters of love.

Here is the thing, all of those articles mentioned are great for general conversation but there is a key thing missing and that is your intention. You should really go in thinking about what you are looking to get done.  Do you want to ask her out? Do you want to feed her some stream of romantic stuff? Do you want to just want to get some small talk in?

You are right to try to cut down on the mindless filler but don't keep talking for the sake of talking. Trust me, you don't want to be "that guy" that keeps some girl on the phone for an hour longer than necessary just by stumbling from one thing to talk about to the next. If you are out of things to say, just get off the phone. Nothing wrong with a 5 min conversation just saying hi.

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