TL;DR: I coached a girl through a pickup scenario with a guy who handled it horribly wrong despite dealing with a very open minded woman who initiated the date herself.

I know this girl (early 30s) from having been in a serious relationship with her in the past. (Our friendship now is very platonic now and we keep in touch to occasionally gossip about mutual friends from the past.) She is a hesitant with men because of some emotionally traumatic relationships in her past, which is frequent topic of conversation with us because she is aware that I am interested in the dynamics of dating and relationships. I won't give her a rating, but suffice it to say that she is attractive to a majority of the men that meet her.

So here is the gist of what happened: She texts me and asks for advice on how to approach a guy she met while running errands. The guy was an employee somewhere and ended up giving her his business card "in case she had any questions," so she thanked him and went along her way. It turns out that she thought he was attractive and did not indicate that that to him in person. Here is the basic sequence of events that transpired (I am going to paraphrase to keep it anonymous):

Girl meets guy, takes guy's business card and texts me "What do I do now? I've never done this before and this seems weird and creepy."

I advise girl to come up with something contextual and funny that also involves a clear indicator that she wants to meet up with him. She does this, texts him, and he initially responds by playing it cool and acting disinterested (she is showing me the text conversation). However, he immediately goes into a "nice guy" beta routine by asking things like "So, where do you want to meet up?" and "When do you want to meet up?" etc. I tell her "You stated your intentions and interest, you let him do the rest. If need be, tell him "Listen, I'll let you be the man and take it from here. Deal?" It did not get that far, but suffice it to say that she had to lure him into the role of being a man. He eventually did and began making plans and being assertive, and she was happy about it.

Then, the next day, he texted her stuff like "Too bad we can't get together tonight"(ish) type of stuff. (There was a 4-5 day delay in meeting up for coffee because she was traveling.) Then, he proceeded to text her throughout the day every day thereafter with stuff like "Good morning, I hope you have a good day" in the morning and "Good night. Sweet dreams" at the end of the day. She was immediately freaked out by it, but she was willing to let the first day of bizarre texting slide since she was so into him and was trying to figure this out herself. But after several days of the texting on his part, and despite me coaching her to not respond or to say "I'm busy, can't talk now", he yard darted the whole situation by creeping her out and acting needy. He eventually gave her the obligatory "Okay, I'll leave you alone now."

Takeaway: Guys can still tank a situation even when the girl herself is needy, relaxed, and being coached by someone who was desperately trying to set the guy up for an easy layup. She indicated attraction, initiated the date, and basically handled every aspect of the logistics for him. She could not have been more willing, more interested, more open minded, or more apt to let his needy behavior "slide," yet he still managed to screw it up.

Don't let this be you seddit, and remember that this guy is your competition when you're talking to women. Let that fill you with confidence on your next interaction with a girl. Be bold, be honest, and assume your rightful position as a man and lead her, and even if she is the one who approaches/initiates. Also, for the love of god, don't incessantly text a woman you just met.

Edit: Just as a reference, the "coaching" I gave her when he started texting a lot was basically to help her understand what might have caused him to act needy, and to keep in mind that he was probably shaken up a bit by having a girl approach him so directly. I was telling her things like "He is probably a great guy who is somewhat inexperienced with women who assert themselves. He is likely in very unfamiliar territory so cut him some slack and assume he's just very excited about the circumstances. Be nice, play it cool, and I bet things will change with him once you finally meet up in person again."