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.
1,000How 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.