Arthur-
Arthur wasn't really sure what you would consider a 'date', it's not like he was going to take you out for dinner and buy you flowers but he wanted to do something that you would enjoy. Then he realised that you would probably both enjoy a casual day out of the camp rather than something extravagant. So he would take you out on a ride before finding somewhere to rest and spend most of the day, bringing some food with you in case either of you got hungry. It was simple but it was perfect for both of you.
Dutch-
Dutch would try to do something special for you, spend some money on you. However this wasn't always easy since he was a found of a gang of outlaws. But he would take you into the nearby town for a little bit, maybe just getting a drink or even a meal at a nicer saloon. He would take you for romantic walks, even if it was just to get away from the camp for some time. He might even take you out to see a show, grabbing a drink before heading back to the camp. Dutch was smooth and somehow managed to make anything you do together special.
Micah-
It would take a while for Micah to even ask you out on a date, and he would be uncharacteristically quiet and awkward about it. Even after you agreed to go out on a date with him, he wouldn't know where to take you or what to do. He would probably just ask you what you wanted to do, and you would both just end up going to the local saloon. Being able to have some drinks together without the camp watching you all the time. It was more than casual but it was nice, it got Micah to relax and you get to see another side of him.
Charles-
Charles would have planned the date before he even asked you on it, just to make it perfect. Of course you agreed to go out on a date with him when he asked you. He would take you for a horse ride until you reached the spot that he had found while he was hunting, he thought that it was absolutely beautiful and couldn't wait to show it to you. You would sit together while he told you stories and about legends, his stories always interested you and always had you listening intently to every word he said. You would only head back to camp when it was getting dark.
Javier-
Javier would definitely take you out of a night, somewhere out of camp, maybe to sit beside a river together. He would take his guitar with him because you loved to listen to him play, humming along with his music. The setting would be romantic, both of you sitting together beside the river and under the moon and stars. Once you were both getting tired and just wanted to relax, you would both just sit there sharing gentle kisses and touches. Both just sitting together and watching the river until you both decided to return to the camp.
Sean-
Sean would be a little shy when he first asked you on a date, which was just not like the loud Irish man. Of course you said 'yes', and he promised you that it would be the best date that you have ever had. Like always, he was overconfident, but he stayed true to his word. It was the best date you ever had, even if it was just a simple date. You would both just get out of the camp and probably get yourselves in trouble. Starting with a short horse race to the saloon, then having a few drinks together, before finding yourselves running from the law or some other gang, not even remembering what you did to get them chancing you. You would both return to the camp laughing loudly, probably waking a few people up.
Hosea-
Hosea would like a simple but a romantic date. Nothing very fancy or expensive but something that he thought would make you feel special, and resembled a date more than a casual outing to the saloon. You would go for a walk, telling stories to each other and trying to distract yourselves from the chaos of the camp. You would probably end the night with a drink and a show before heading back to the camp.
Requests?