That is a terrible situation. I definitely agree with Esylum as you both need to be there and bluntly tell him together. I also think you need to go a step further and either cut ties completely with him or tell him if it continues you will cut ties with him. If he was to try to continue you and your wife may need to go talk to his wife about it....and be sure to cut ties with him. He may be entertaining at card games and get your competitive juices flowing....but is it worth letting him be demeaning to your wife? On the other hand...if he does stop his advances and you can better your friendship....your wife probably shouldn't be sending him any kind of texts or any other things that this man could take as an advance towards him. He obviously can't tell the difference between an innocent joke and something more.

Just my honest opinion. Best of luck to you and Chris! Keep us posted!