We all know women dont like boring guys. we have to be memorable, not boring and forgettable. to do that, we are supposed to say something bold and ballsy.

the problem is, oftentimes I am afraid something is inappropriate and won't say it. But then this turns me into a boring guy and the girl leaves. I cant tell if something is inappropriate or courageous.

I will give a simple example. "do you have nice boobs?"
is that ballsy? will it make me look like a confident, memorable guy? or is it rude and will make me look like a prick?

I guess it depends on the context. If you have been talking to a girl for a while and the attraction is there, then the question is great. but you cant walk up to someone and ask them that. But the problem is, I won't be able to build that attraction without saying something ballsy, can I? so this creates a vicious cycle where I cant build attraction because I dont want to be inappropriate.

edit: this is not all about "saying" things. It's also about "doing" things. For example: "is it inappropriate to touch her now?" "is it inappropriate to kiss her now?"

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I have not failed 10,000 times. I've just found 10,000 ways that won't work. - Edison

The difference is in whether you ask yourself "is it appropriate?" or not. I used to do the same thing, and I lost a ton of opportunities. I've changed that mindset, and a good example would be how I got attraction going on the dance floor. Before the change, I would usually just go on the dance floor and wait for a miracle to happen, maybe get into a group of girls and try to fit in. A week ago, I pulled the girl pretty much everyone was drooling over next to me and she not only didn't mind, but also started grinding for the remainder of the night.

TL;DR: It's inappropriate if you think it might be, it's ballsy if you just do it without thinking of the consequences.

P.S: Of course there is a limit, but you can get away with pretty much anything if you are confident enough.

I wouldn't say that if you are at the AFC stage right now. One of the things that you learn in RSD is that you can say anything if you are in state. There are certian negs (if you follow MM) that you can use that are pretty ballsy like "I bet you're one of those girls with wierd shaped tits". I haven't used this myself though.

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You can be ballsy and inappropriate at the same time. The problem is when it comes to a ballsy statements. A majority of the time a ballsy statement borders on inappropriate. The person who decides on what's appropriate and inappropriate is your target. So your question, "do you have nice boobs?" may be okay for one woman and not the next. I'm pretty sure you would be on damage control if you asked most women that. But if you really wanted to get to that part of the conversation...you should reframe it so she's the one making the statement about her physical qualities:

You: What part of you physically attracts the most attention from guys?

Asking this will deflect anything inappropriate said by you and have her talk about her physique. More than likely, she will answer by saying something like her eyes. So you have to eliminate that option after she answers by saying that guys always say the eyes but we're lying and ask the question again. Then she'll answer the question and at that point you'll be allowed to make your statement and she'll be open to hearing it:

Her: I would probably say my boobs.
You: You know what? I probably would have to agree with that. (If you are comfortable/confident enough, you could actually disagree with her and say her ass may be better)

At this point she mentioned her boobs first and you are just piggy backing off of the statement she made.

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Or you can present her with such strong alpha male energy that there is a trickle running down her leg. Your eye contact, presence and demeanor makes your intent if the two of you are ever alone very clear. You stand out from the masses, become very memorable and she looks forward to seeing you again.