I am friends with this dude. We're each other's wingmen but he is an ultimate beta. A while back he broke up with his GF and was devastated. he would do anything to get her back. I am friends with said ex and I am also a professional translator. She contacted me a very casually and asked me to translate 100 pages for her. It was a lot so I quoted her with the estimated price, it was kinda high. I told this guy about it. he and his ex still kinda see each other in our social circle. He said "dude when we see her I will tell her I will pay for the translation so I'd get her attention and I'll become the good guy and she'll see that and takes me back" [UBER CRINGE]. I said okay I don't care then he said "but I can't pay you that kind of money can you do it for free?" I politely declined.

Today he came to me and said "I was kinda offended that you wouldn't do that for a friend, after all, we've been through a lot together". I persisted it was a lot of work and just couldn't do it for free. He wouldn't back up. I changed the subject.

Normally I would tell this kind of person to fuck right off, but this guy has lots of uses (beside wingman) that I would rather not lose.

How do I proceed in a manner that wouldn't end up doping the nuke on him? Cause I need stuff from him for now.