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.
1,000
@Ceces couple of questions.
1st are you a man or woman
2nd how high will both your standards be? specifically in respect be to get laid.
upvoting all the “he gets laid” options for good luck!🍀
as for the pickup line suggested in the comments, I’ll kick things off with “Hey babe, my ex made a prediction market about whether I’ll get laid this week. Wanna frontrun the rally together?”
I’ve found you gotta go niche on these things
How much does Tony want this?
I’ve seen wingman attempts fall into equilibria where more attention is given to the wingmaner than the wingmanee, which can lead to depression spirals, rejection-sensitive dysphoria, etc. Have y’all talked about this possibility? Do you want to come up with a plan for what to do if this happens?
@KJW_01294 i think the attention issue won’t be as much of a problem since my wingman is a girl (although that can cause other complications). In general I’m not super sensitive to rejection, I get that dating is mostly a numbers game and about finding compatibility, and I feel secure in being single at the moment.
@KJW_01294 I have 3 years of experience helping my other friends by wingmaning and I have mastered the art of making myself disappear once the conversation picks up. I can also help with rejections as while I have been hit on and I rejected, I have also been rejected. I think the goal is to respect rejection and rolling it off your back. Which means you can’t get attached to someone immediately or take said rejection personally. Tony is pretty pragmatic and logical making it easier for him to overcome these mental obstacles.