#sparklingapplecider

I like to think that Cuphead (and Mugman) have been friends with Mac all the way back in kindergarten. In fact, Cuphead was Mac's only friend for a long time. Cuphead taking notice of Mac's drawings is what led them to talking and having lunch together later that day.

Mac and his Granny Smith have been the cups neighbors for a long time too, however he very rarely came over to the cottage. Cuphead would go to him, either in his backyard or the crick, it was mostly down at the crick. Cuphead still would never openly admit that Mac made him feels things but it wasn't easy to deny when he started seeing him at the crick almost every weekend. At least to Mugman. Though he promised Cuphead that his secret would be safe with him.

While Cuphead and Mugman were collecting soul contracts, Mac (along with Canteen) wouldn't be far behind them. Whenever Cuphead or Mugman got hurt after a fight he would be there to help patch them up.

When Cuphead and Mugman set Ms. Chalice free from the urn Cuphead had never been so captivated by someone's beauty before. He would never admit it to anyone but Mac about how he felt about seeing her. Mac would even draw her for him. At first, Cuphead did feel a little guilty whenever he talked about her, he could tell that it made Mac a little jealous about how beautiful he found her.

With the help of Chef Saltbaker and some tour guide they brain washed/hj, Ms. Chalice got a chance to call Cuphead and Mugman to the fourth Isle to help in the making of the wonder tart, and Cuphead got a chance to make a formal impression on the ridiculously beautiful lady ghost.

Both the cups were amazed by Ms. Chalice and her fighting skill, but Chalice didn't start to feel things for Cuphead until he took a hit for her and saved her for the first time. Mainly because nobody's ever almost died for her.

DLC events and other stuff you've already heard later.

Cuphead and Mugman are on the boat ride back with Ms. Chalice. It's a few hours before the three are greeted by Mac and few other friends that promised to wait for them. You know how I said that Mac would get a little jealous whenever Cuphead would talk about how beautiful he found her? Well he was right to be so, at least that's what he thought.

I think Mac was almost as stunned by Ms. Chalice as Cuphead was. Even in the dark of the early night, he couldn't even say anything to her. It was a little awkward. The injuries that left scars were taken notice of the morning after when Mac came to check on them and see how they were doing. Ms. Chalice ended up with a scar beside her eye that damaged her vision.

I have this headcanon that Mac is blind in one eye due to an injury that he suffered when his was little (he was bit by the dragonfly in treetop trouble) I also think that Cuphead also ended getting half his face blown off when him and Mugman fought thier way through the casino and also had his vision damaged

As Chalice was struggling to adjust to it, Mac (very awkwardly) said that the three of them match. I think it was an awkward breakfast, especially for Mugman. Chalice thought he made a good first impression.

I think that both Chalice and Cuphead were taken back by Mac's awkward sweetness but she was a little more comfortable with his open affection than Cuphead. Ms. Chalice almost couldn't stop talking about him on the walk home.

I don't think that Mugman realized that Cuphead was having feelings for Mac AND Ms. Chalice until later on. But I do think that he would flreak when he did find out, and wouldn't stop talking about it to Cuphead whenever Chalice and Mac weren't around

The three wouldn't have "date" dates but they would often go to breakfast or lunch, maybe even to the carnival, or out of sight on top of a food vendor or something just to talk. I think that Ms. Chalice would model for Mac, he would draw her wearing anything she could sneak out of an expensive store. I think that she would be able to get Cuphead in on it too. It would be boring as hell but it would be worth it to see the final product.

Cuphead and Ms. Chalice would sometimes use training thier powers as an excuse to show off how powerful they are to Mac. They would get competitive with each other too, half the trees in the woods would be gone as a result. I think that Mac would want to draw it but would be too amazed.

I think that after defeating the devil and detours and the events that occurred on the fourth Isle, the three cups gained some popularity in Inkwell city, and eventually the three were looked at as heros. But not everyone thought so. Sometimes, very rarely, the cups would end up in an unsafe situation with the people who saw them as anything but good people. I don't think that Mac would be the only one to protect them but he definitely has to to it the most (right next to Elder Kettle and Chef Saltbaker) Mac and other friends like Canteen would often act as the cups bodyguards. He would always be very insistent on being with one of them because he wanted to keep them safe.