Friday, November 17, 2023 – New York City

She was Afro-Caribbean and had come from the UK to study in NYC. 5’8″, dark-skinned, introverted, feminine, braces. I had approached her two weeks ago coming back from class. I remember it being a solid set in the moment, just under ten minutes long.

The texting went smoothly and I asked her out, but she said she was too busy to meet that coming week. Stupidly, I archived the text and forgot all about it. I place almost no stock in texting these days because of my horrific text -> date conversion rate (I’m currently at maybe one date scheduled in the past 50 to 60 numbers).

This evening, I accidentally reapproached her not two blocks from where we first met. Her jaw dropped immediately as she recognized me, and I realized she was the British girl from two weeks ago. I teased her about stalking me and then about being “busy.” She revealed she had just taken a big exam and offered up that she was free right now as she was just wandering around after school. I told her to walk with me and led her to the nearest park.

I could tell this girl was attracted, but required large amounts of comfort. As we got to know each other, I focused on avoiding therapist frame and instead getting her to open up by sharing stories about my life and about people I knew. This has been a sticking point of mine and while I still haven’t achieved the level I want to be, I’m happy with my effort.

Our conversations spanned geography, music, fashion, family, and cultural differences. She revealed that her parents were not strict, and true to many people with non-strict parents, she wasn’t much of a rebel. She hadn’t tried drugs other than weed and mentioned that she was “new to all this” when I brought up dating. I thought for a moment that she might be a virgin, or at least had very little experience.

She had her arms crossed so I called her out on it and she laughed and said she always does it and shouldn’t. I used the opportunity to grab them and play with her hand. There was no resistance to this.

Just before 7 PM, a park worker came through and let us know the park was closing. I had seeded my place a couple times in the conversation, so I said I had an idea and she was down with no hesitation. Walked her back and she sat on the couch immediately. Good sign. She liked Dean Blunt so I put him on.

Within 15 minutes I had her standing close, my arms wrapped around the small of her back. The kiss was accepted enthusiastically. I thought about pulling away, but there were no games here. We were in the moment. Undressing her revealed a body — long and lean with abs and a tight ass, an always welcome surprise among NYC black YNDs and their baggy clothes.

As we got on, I could tell this was no virgin, and no lack of experience. This girl was built for abuse, and she took punishment with seemingly no ill effect. Another secret freak in an introvert shell.

Suddenly, though, as she started riding me, things started to feel a little too good. I couldn’t control myself while wondering what sort of godpussy this girl possessed. After a minute of post-coital bliss with her draped over me, the answer became clear:

The condom had broken. Ruptured right through the tip.

I swear, this must happen to me more than any other guy I know. I’ve gone through many brands now: Okamoto 004s broke on me, now the Okamoto Winks are banned. I’ve tried a couple others that I didn’t like but may now have to go back to.

I told her it was OK and that I’d give her a morning-after pill to take (they’re $7 on Amazon, recommend having a stockpile). This is where things took a turn.

I went to wash up and she was suddenly quiet. She started putting on her clothes. I tried calling out the frame, but my air was more flippant, like “don’t worry about it”. I wasn’t attuned to how freaked out this girl was. She took the pill and I assured her that everything was going to be OK.

The vibe was completely shifted at this point. I asked if I should walk her to the train station and she said yes. I tried to be fun to take her mind off things, and when that didn’t work, tried asking her questions, but she didn’t bite. We spent most of the walk back in silence.

It was a bitter end to a great connection and a great evening. I really enjoyed our time together, and would have loved to see her again, even though the chances were slim anyway (it’s NYC, after all). But the vibe was irreparable, or so I thought.

What I Should Have Done

I brought up the situation to my wings.

John Adams suggests trying to get her perspective on it during the parting:

“Hey, I had a really good time tonight. How do you feel about what happened tonight?”

It reaffirms in her head that the one bad thing didn’t ruin the whole night. If she answers in a negative way, you could still address it.

“Look, I had a really fun time, I didn’t mean for what happened to happen. I’d really love to see you again.”

You have to sell it and feel it. You have to force a moment of realness.

“I know you’re in your head bout the condom breaking, but can we actually talk about what you’re going through, I hate leaving things on a sour note.” (Lean)

Dante’s example:

“Hey, hey, hey. Listen. Calm down. I get what happened. You trust me, I trust you. That’s why we’re doing this right now. Everything is going to be OK.” (Hold her hand and kiss her) “Don’t worry, I got you. I apologize. This is not going to happen again, we were just having fun and we didn’t know that this was going to happen, so you’re going to be fine. We’re here together. We’re in this together.”

What happened is that I froze and went back to my normal detached emotional state where nothing matters and everything is going to be fine. But she stopped being connected to me when I was like that.

Next time something like this happens, I need to force a moment of realness, even when the girl won’t open up.

Who knew that the learning moment of this close would happen after sex? I need to be prepared to deploy Game, always.

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