Hey How_R_U,
Again, nice work! Though now i got a bit more remarks about the convo's, so lets break them down and see where we get.
But first, i'd like to come back to the post of RR:
Quote:
I know, I'm from the boyfriend replacement bureau - they said it's time to upgrade.
Hehehe, i like that one
Quote:
Awww... How cute - you have a boy friend. a BOY friend. Darlin - I'm a grown-ass man. You should find a MANfriend
and that one as well.
But... and this is actually a remark towards How_R_U as well: this is not really direct anymore. This is more like cocky funny with balls. Although you want this in your interaction, it is not direct IMO. But more of this when i get to the convo's.
The conversations:
In general i can say that again that what you say is not really congruent with what you want (or want to say). You are talking around the bush (or how goess that saying again?)
First converstation: I tihnk this is a nice opening, but you arent really interested in what she is going to buy. She cant really show herself in a unique way either.
You want to tell her that you think she looks hot and you want to do stuff together.
But instead, you do ask more about the makeup. She kinda knows you arent there for the makeup. So what are you hiding?
Better might have been (and yes, i know, its easy saying from behind my computer

):
you: Hey, in case... too often.
Her: okay (laughs, bit shocked)
You: (what you want now is to look her in the eyes, so if she is not facing you anymore, you just say:) Hey.... (she looks at you)... you are actually very pretty. Why would you need make up? (here, you really need to shut up. dont let her off the hook. You are making a statement, and you are man enough to take whatever she answers. It needs to show you are that confident).
she:... well... you know, i need to look good and all the women do it.
you: Hah, yeah, all the women do it. But i like natural girls more. Most beautiful girls wear make up to hide their personality. (again, silence

)
she: (this can go both ways here as you are quite firm and seriously qualifying.) *bitch reply*: yeah well whatever
you: hmm, i see now why you need make up.
*not bitch reply*: oh, but i am an interesting girl (smiles)
you: really? well, lets find out then! Tomorrow, 7 pm, lets go for a quick dinner and a drink
second convo: this has happened to me often enough. Good looking from far away, but far from good looking. Exit asap

.
One thing though: you talk about transitioning. FUCK TRANSITIONS. Be aware of the context of the interaction, but fuck transitions. State what you want and say what you want to say. Transitions are usually an excuse for not saying what is on your mind. You keep on looking for the good opportunity to say what you want to say,
but there is no better time like now.
Third convo: nothing to say

. She didnt want to reply apparently.
Fourth convo: if she stops walking but just says thanks, you should keep on going.
if she didnt stop, you could say hey wait! and then be super direct. But the fact that she kept on walking should already tell you enough.
Fifth conversation: I can understand you felt kinda set back by the boyfriend reply. But you can work with it. its not because she has a boyfriend that she isnt available. And another thing i want to say first is, again, you didnt really say what you want to say. you arent really honest nor direct here. I know you know that the weather subject was not that good of topic

, but it is because you are not telling what you want to say that you end up in these weird 'shit test like' situations. It feels like you get slapped in the face by sheer logics. 'Well move back then'. sheer logic. If you were really honest with her, and not set back by her boyfriend reply, you would not have any trouble with this question. I hope i make sense here, but if not, ask

.
Ok, i would have done the following:
you: so where are you going?
her: to my boyfriend
you: oh, that is too bad. Wel for me anyway, as i think you are cute and i actually want to get to know you. I was going to take you out for a drink

.
You answer here with plain honesty. its a smacker for her. if she really got a boyfriend, she will say i am sorry, but i cant. Then you know she really got a boyfriend or she really isnt attracted to you.
If she does say ok, where and when, dont say anything about the boyfriend. Ask her when you see her again. you will get an honest reply then.
Through experience, i know this works way better then C&F replies. Yes, there you are, naked and ready to get gunned down, but it takes a lot of balls to go like this and most girls will instantly respect you because of your honesty. I like the reply examples of RR, but they only give the girl an impression of your intentions and of what you really want. Which puts them on alertmode, they are cautious and sometimes not at ease.
Every once and a while, you will be very open and honest, and the girl still will not be at ease. Never mind that, go with her emotional situation and show understanding, like: hey, i know this is kinda awkward, but if you saw an opportunity for something you really want to do, and the next second it would be gone, wouuldn't you mind the awkwardness?
something like that

.
You are doing good. be pride my man, because you are walking the path! Its the best way of learning and the most fun!
Also, i know the kicks in the nuts hurt. And actually, i am happy you received this kind of kick while you are doing just an approach and not yet fully direct. You need to get used to these kicks. its always better to get the kick and now it aint gonna happen then walk past by her and always wonder how she would have reacted.
When you go fully direct, more in the direction like in my examples, be prepared for kicks that seem much more painful. Its is because the nuts are larger (figurally speaking). Honesty is great seductive weapon, but it cuts on both sides.
good luck mate!