Date Report 002 – The Italian Waitress

My dream girl from the eighties – Valeria Golino

I met a girl at Museum Station – an Italian – who made strong eye contact with me as I walked past. Strolling up the street on my way home, I decided to turn back and speak to her. She seemed Brazilian, with a pair of filigrain silver earrings, a birthmark on her face which looked like a tattoo, curly brown hair and dark brown eyes which kept contact with mine.

She said she was Italian, not Brazilian. “Better”, I responded. “Nothing more Latin than the home of the Latins”.

I got her number, exchanged a few texts as to why I was all in white (she suggested baker or gelato maker), and I agreed to call her the next day. We talked and set up a date at a place in Kings Cross.

I arrived late; she arrived later; took the endless stairs to a rooftop bar and ordered drinks. I liked her banter, her talk, like a game of tennis (or even faster – badminton) where every comment would be countered. Jokingly, she said she would be exhausted for a week after the date because of the banter and need to sleep it off.

The vibe was on, we chatted freely, she joked about running a pensione brothel in Italy, compared our “best stories”, and I asked her if she had ever been in a strip club. She was categorical in her answer – no.

I regaled her with a story of travelling in the back of a truck with paramilitaries in Colombia; she returned the challenge with a story about being harassed and harangued at an airport and accused of being a drug dealer.

She was 30, talked about her “bad days”, and said she’d be resigned to the Inferno (or Hell) because, well, Dante’s Purgatory or Paradiso were just boring books. I was surprised, a woman who read as thoroughly as me. We talked about Umberto Eco (boring), Harry Potter (I have never read it so it was a -1 point for me) and how the ending of Game of Thrones would disappoint everybody.

I never really felt she was open to me making out with her except for one small moment (which I missed). Time after time I have felt a crackling sensation in the body when I knew it was on – a signal to make a move … but I faltered and kept to myself.

She later went into a deep rant about the state of men in Australia, a beautiful picture but without passion, skin deep, and she had to be pulled out of these dark thoughts by me. The window to escalate had passed. I think the date was to test her theory as I sensed she had never been with an Australian guy.

I shared with her one insight about Anglo-Saxon culture – it suffered from a failure to feel. When we feel something deeply, we deflect it with humour or a stoic outlook. It was an attempt at deep rapport, genuine connection, but felt the vibe was going and did not know how to save it.

Ordering the last round of drinks, the Italian bartender recognised her and asked whether she was the same girl who had worked at one of the strip joints up the road. She seemed miffed after that, the bubble had burst, and she had been caught out as a liar. She was a waitress there.

I didn’t care – the purpose of my life now is to be non-judgemental and let women feel free with me – but it bothered her.

As we walked up the street – her to go home, me to go to a music jam – she made fun of a man in a cardboard box and called it camping. I challenged her and told her to be more empathetic to suffering. Weird comment but a person’s values shine in those moments.

I had given her an imaginary card – one which gave her a free pass to ask me any question to which I would tell the whole truth. I told her it would expire at the end of the night and she would need to return it if she didn’t want to see me again (lest it be sold on the Dark Web).

As we got to the intersection, we saw a billboard of Positano with a large Aperol Spritz. I told her I had been there and she called me a liar. I challenged her and said she needed to kiss me if it were true. She balked and said she didn’t agree with the challenge! I knew it was off from then.

Then she returned the imaginary card with an apology, telling me she had had a good night and she didn’t want to see me again. And that was it. She left.

Later I sent her a photo of my son and I in Positano …. she responded “So it was the truth!”

Ah the irony.


1. Take advantage of the tingly sense in the body as an indicator of when to make a move.

2. The bubble was burst when she was made out to be a liar to hide her past. I truly didn’t care … yet my respond to her was to gently chide her for not telling the truth. I don’t think she genuinely believed it and may have gone into auto-rejection mode from there on in. There was no way to re-inflate the bubble.

3. A strong identity does not need to hide the truth. While I think men should be calibrated to not completely share their story at once, I feel that a proper and unabashed frame requires complete acceptance of your life – warts and all.

4. The faster you get to a rejection, the better. While there are lessons learnt about women during each stage of the seduction process, it can be infuriating when it comes after spending your valuable time with a woman.

3 thoughts on “Date Report 002 – The Italian Waitress

  1. Good tale, and good insight.

    I think its hard for us (guys) to understand how painful it is for a woman to get called out like that. Particularly if she had been educated at some point and then fallen in status to working in a club. You might not care but she does.

    I have certainly glossed over similar moments and thus let the interaction die, and the relationship die. The PUA response might be to enthusiastically say ‘Hey, you had me beat – that was a way better fantasy. Tell me a new one.” But I don’t think it works in this case without a lot of booze. The new age response would be to just call it out and say “wow. everything just changed didn’t it. … I like _______…” Where you notice something that gives you reason to continue. You must have liked something as you didn’t walk away. Then you can let her tell you something real or you can spin into the whole ‘stories that we tell ourselves’ loop, and thus spin a new bubble that is both a bit more real and a bit more meta.

    Next time!


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