I am @TonyPepperoni’s ex, and he is struggling. I am visiting downtown SF and we are going to go to some bars from 06/11-06/14. I am trying to get him as many dates as possible.

On a typical night out, I get about 1 number, 2 compliments and 2 free drinks, all from different people. On a typical night out, Tony doesn’t go outside, he is a goblin.

I enjoying dancing and chatting and I am fairly outgoing. Tony stays inside. But I believe in him! 🤠

Neither of us will bet on this market.

• Update 2025-06-10 (PST) (AI summary of creator comment): The creator's evaluation of 'how well' they wingman will consider aspects beyond the number of dates, including:

  • Their skill in making themselves disappear once a conversation between Tony and someone else picks up.

  • Their ability to help Tony manage rejections effectively, fostering an attitude of respecting rejection and not taking it personally.

• Update 2025-06-11 (PST) (AI summary of creator comment): In evaluating 'how well' they wingman, the creator has specified that their standards, and Tony's, for interactions will be 'a bit higher than average'. This will factor into their subjective assessment of their performance.

• Update 2025-06-11 (PST) (AI summary of creator comment): In relation to a potential market answer where the creator gets laid, the creator has clarified the circumstances of such an event:

  • It involved someone they had been chatting with for a few days prior.

  • It occurred when both individuals arrived at the SF airport at the same time.