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The most difficult pick up ever

TrailBlazer

Space Monkey
space monkey
Joined
Aug 15, 2025
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88
At the lowest point of my past few years, I saw an offer for an anxiety coaching program in my university. So I signed up for it. I had long fallen out of my day game streak by then and didn’t have enough energy to get back to it. So I secretly I hoped my coach would be a young woman I could train my seduction skills on.

And a young woman it was. Very friendly and bubbly, although a bit melancholic. For the first 8 months of our weekly meetings, the vibe was friendly. I used to be quite needy with her too, she was the only person I was meeting and often ended the meetings first, and I often asked her to spend more time with me (either directly, or via manipulating her by telling her the coaching is not helping me at all).

A few months back I started feeling good again, so I started with daygame again. I became better at holding tension and the meetings with my coach became more charged. We talk about sex a lot.

On one of the more recent meetings, I started touching her more (with the excuse of showing her some tantric stuff). She told me she thinks about me often.

Here I asked her out outside of the program and she said yes, so I succeeded in breaking some of the boundaries.

However on the secret meeting I was too scared to escalate and so nothing happened.

Since then we saw each other officially like 3 times, and she is still kind of receptive, but not as much as before. And I’m still too scared to escalate too much.

However I’m determined to making this work.

To make this post a proper FR here is our latest meeting:

We met for a coffee, I stacked compliance by telling her to do various things, I built attraction by using more sexual gambits, and then I showed her another touch routine. I also showed her an event we could go to together, but I was too scared to invite her directly. But maybe I did it right, I’m trying to minimise the No’s I get and I know her quite well by now to know what will work and what won’t.

Let’s see where this brings us. Please just don’t try to talk me out of this challenge. I was almost there a few meetings back, so it is possible. And the idea of picking up your coach is quite co
 
you miss 100% of the shots you don't take
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