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(Editor's Note, this letter was written before Doc's death in August, 2020 but still relevant as Doc's principles are timeless).
I’m an avid fan of “The System” and I read your articles every day during my lunch break. I think you’re doing a great thing for all men by coaching us with your valuable knowledge. However, there’s one subject that I don’t think you cover directly. How do you persuade a girl who is a casual acquaintance to go out on a date without looking desperate or overly eager and at the same time maintaining Challenge?
I am currently a college student who is very sociable and quick to meet and greet people, especially females. I met Anoushka last year while going out with a large group of friends. We chatted, had a few laughs, and exchanged phone. Truthfully, I sensed no spark between us and only asked for her number so that I could brag about it to my friends. Also, Anoushka was in a relationship with someone at the time.
One year later, Anoushka is single. My dilemma is that although I’m dying to strike up a conversation with her and ask her out on a date, I’m not sure how I should go about it without looking desperate. We have not been talking regularly at all, just occasional greetings whenever we see each other on campus. I would try and just give her a call and ask her out but I feel as though the conversation would be awkward since we’ve not had a real conversation in person in about a year. I would also try striking up a conversation when I see her around campus, but I’m stumped as to what I should talk to her about that would smoothly transition into an invitation for coffee.
Another big problem is that Anoushka has three friends who she’s constantly with and I rarely see her by herself. I really don’t feel like trying to figure out how to separate her from her friends. Every way I think to approach her makes me look too aggressive and not challenging at all.
What should I do? Did I miss my chance by not staying in contact with Anoushka for the past year? Should guys always stay in touch with a girl who has potential even if she’s not immediately attracted to him?
Drake - who’s stumped
I do cover the subject of asking out a so-called “casual acquaintance” in my book, but you must have missed it. But that’s okay. We’ll cover it again. Asking this girl out is a piece of cake, so don’t worry.
Your ability to meet and greet females and chat them up is a great quality, pal. Most guys don’t have it, so you should be grateful. Let me compliment you on that. It can take you far with women.
I have to hand it to you, Drake. Getting Anoushka to give you her number so you can brag to your friends about it shows that you’re really mature, ugh. Like the old cowboy saying goes, “It’s a step away from notching your belt.”
Now let’s take a look at what has you bent into a pretzel here: asking Anoushka out for a date without looking desperate. It’s simple, dude. Just do what I tell you to do. You have the vastly mistaken notion that any forward move toward this girl is going to be seen as desperation. But not if you go in slowly.
The fact that you haven’t been talking to this girl on a regular basis has nothing to do with anything. The point is that she’s comfortable with you and she knows who you are. This gives you an advantage. Use it.
Why would the conversation be awkward if you ask Anoushka out? Just because you know her? Forget everything that happened between you and this girl in the past. When you call her up, act like nothing’s ever happened between the two of you. And then you’re going to ask her out and start finding out her Interest Level – if there is one -- which is the whole idea of the Starbucks date.
If you’re stumped about what to talk to Anoushka about leading into asking her out, just ask what classes she’s taking in college.
You’re not going to pull a divide and conquer with Anoushka’s friends. Like my cousin General Love says, “You’re going to do an end-run around them!” Let me say it again: you’re going to call Anoushka on her cell phone and you’re going to make a date for Starbucks. Forget about her friends, and forget about the fact that you know her. Like I said earlier, none of that stuff matters.
See, Drake, you’ve got something really mixed up here. It’s a mistake to think that any action in the direction of this girl is anti-Challenge. I teach you to make that first move. I coach you to ask for her phone number. I tell you to kiss her on the date. To you Psych majors, these are confident, aggressive moves. But don’t forget, prior to doing any of that, you’re making her laugh 99% of the time. Keep it light and keep it funny. Along with moving in slowly, that’s an essential part of your battle plan.
It’s better that you didn’t stay in touch with Anoushka over the past year. Because now you’ll have things to talk about. Staying in touch with a girl who’s got a boyfriend is a waste of time and effort.
Remember, guys: if you’ve got her phone number, just call her up and ask her out to Starbucks.
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