“And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.”
Anais Nin (1903 - 1977)

So a ways back I posted something that people seemed to dig. Now I’m posting something for someone like me. See before I had the confidence that I have now…I was the type to pine for a woman. I had a lot of trouble breaking that friend barrier. More then that it took me a long time to be able to just approach a woman. Truth be told I still get ansy. So here is the scenario:

You’ve been around this girl for a while, you’re digging her. People say there is chemistry there and she seems to have some interest. Problem is you may fumble like Kyle Boller with a lead in the 4th quarter (I can say it, I’m a Ravens fan and I’ve supported him). How do you initiate?

1) Preparation - So you’ve been around each other for sometime and have not made a move. This is a double edged sword. On the positive: You haven’t come off as a horny asshole that asks every girl for her number and if you weren’t with anyone else during this time there isn’t much info floating around about you. Downside: Extended time puts you closer to the friend zone. You need a fact finding mission: You don’t want to build yourself up to do something to get crused by the truth that she has a man. Use your resources to find out if she is seeing someone. Mind you asking lots of people is a bad move as word will get out. Even asking one wrong person can sink you. I once had a guy ask me what I thought of a girl then go tell her I liked her. Mind you it was in high school, but assholes grow old, they don’t usually mature. If someone you can trust may know ask them. I always like to know what I can beforehand whenever possible. If not one thing never fails…

2)Ask Her - If you want to talk to a woman and you get nervous, the best cure is to get her talking. The point is to get you talking really, but if she’s talking it makes it easier on you. So just ask her, “How are you…How the fellas treating you?” It’s innocent enough, but if she’s open you find out what you need to know and you learn about her. Chris Rock was right, you’re looking for the combination of words that will allow her to talk. My lady…(Hey Vixen) related some stories about the lame dates she had been having and the lame approaches that dudes were making. I used that chance to relate how I thought things should happen and after I made sure she was someone I wanted to deal with I gave her this advice about a frequent caller: “Next time he calls tell him you met a guy who’s loved by children and animals and go out with me.” Needless to say it worked. Not because I’m charming, handsome and actually loved by children and animals (even though I am), but because in the lead up we had talked in a way that let us know about each other. I became sure that I at least wanted to find out more and she was fairly certain I wasn’t totally crazy. She has since discovered I’m about 20% crazy…an acceptable level. To put it in perspective all of the prior conversations happened in a group of friends. So it wasn’t an obvious thing, it was simply people talking about the insane world of dating. Groups can be bad if you blurt out “I think I love you.” If you just talk about relationships and dating it’s the safest way to find out about a person. On the otherside, asking on the one and one opens the door to you openly flirting, without you having to.

3) Your Move - If you can get this line of conversation moving it’s your chance to show her who you are. If she has a beef about something dudes do then tell her how you handle the same thing. Mind you…Do Not Lie or Tell Her What She Wants To Hear. If she mentions something don’t just be critical of these guys. If you think you have insight to their motives share it. Lying is never the move though, if you get with her she’ll remember how you said you thought dudes were fools for doing the thing that you’re currently doing and she’ll be pissed. Also it can be a chance for you to examine things you’ve done and see how women receive those actions. The point is for both of you to learn about the other. If she goes off about how she needs a man to pay her tuition and increase her wardrobe…you’ll know to back off. If her biggest beef is that people don’t seem to have common sense, you know how to approach. Don’t forget you want to know more about her…that’s the whole approach.

4) Mantra - The Goo Goo Dolls had a song I loved called Iris…yes I can be sappy. One line in particular stood out to me because it’s the truest thing you can do. “I just want you to know who I am…”. In the end that’s all you’re trying to do, is make sure she knows who you are. Hopefully it means she’ll want to be around you once she knows. If not, well it sucks, but at least there is no confusion. When all else fails if you can’t think of anything to say, I think that is the most appropriate thing to say. You want to retain your coolness. By coolness I mean:

From Websters -
2 a: marked by steady dispassionate calmness and self-control a cool and calculating administrator b: lacking ardor or friendliness a cool impersonal manner c: of jazz : marked by restrained emotion and the frequent use of counterpoint d: free from tensions or violence meeting with minority groups in an attempt to keep the city cool

Synonyms: cool, composed, collected, unruffled, imperturbable, nonchalant mean free from agitation or excitement. cool may imply calmness, deliberateness, or dispassionateness kept a cool head. composed implies freedom from agitation as a result of self-discipline or a sedate disposition the composed pianist gave a flawless concert. collected implies a concentration of mind that eliminates distractions especially in moments of crisis the nurse stayed calm and collected. unruffled suggests apparent serenity and poise in the face of setbacks or in the midst of excitement harried but unruffled. imperturbable implies coolness or assurance even under severe provocation the speaker remained imperturbable despite the heckling. nonchalant stresses an easy coolness of manner or casualness that suggests indifference or unconcern a nonchalant driver.

The things in bold are the true cool. See, the biggest problems in these situations are:
1) Being too aggressive.
2) Pestering.
3) Lack of confience.
4)Not taking action.

You want to present yourself and demonstrate your worth so she can make up her mind. You don’t want to keep asking and pushing. What you want to do can be broken down into three basic steps:

Forget that you dig her and just find out who she is.
Let her know who you are.
Give her space to make up her mind.

These are my same three rules just in lay terms.

Going to dinner or whatever is just extra. All you really want is the chance to talk. Where you take somone is just further demonstration of your personality and taste. You have to understand the three rules so if you tell her you want to know her and for her to know you it is (and comes off as) genuine. If you have trouble finding actual words to initiate the process, keep it simple. “I’m curious about you.”, “I think I want to know you, but I’m not sure.” (explanation being that she seems cool but could be hiding her crazy), “What are you doing right now, would you care to join me for a…(drink, cup of coffee, whatever). If she’s chilling some where: “Do you mind if I sit with you”, if she says yes warn her you might start a conversation. Keep it light. Even though it feels like it this is not the Apocalypse…remind yourself of this as well. She is a person just like you. As cruddy as this sounds this may bring the last point home:
She has gas.
She takes dumps.
She probably has bad breath when she wakes up.

Just like you, me and everyone else. When we like someone we tend to build them up as we’re seeing good things about them, you don’t have to reduce her to nothing in your mind, but remember she’s not infallible. That means you don’t have to be either. Joke with her about how clumsy you are. Tell her you’re 6′ 4″ and can’t ball.

Deliberateness is your ally. Don’t happen to be somewhere and see her. Your intention is to talk to her. Don’t pretend “Oh, off the top of my head…”. You don’t have to say, “When I saw you today I had to come and find out about you.” But you don’t need to hide this fact either. You had a plan and you planned to see it through. There is nothing wrong with being transparent. Confidence makes just about anything cool…except explosive diarrhea.

Most important: Do something, talk to her. Nothing worse than wondering about outcomes that could have been.
Would any of you ladies add anything to this?