Not a big fan of matching pipes to bodily features, clothes and occasions, as mentioned in my earlier post. But if you are trying to do that, it's an exercise in fashion thinking, so I guess you have to go there. You can play it for consistency, getting the pipe to look consistent with your face, long or round or square, and commensurate with the occasion, formal or folks or whatever. But then there are all kinds of cross currents you can perform, like doing a cob pipe with a tux, or an opera pipe with jeans. If you get into "acting," you'll have to try it in the mirror. Dating, I wouldn't do a churchwarden. That's an indoor, sitting down pipe, and you can't do that out on a date, only later when you are comfortable being at home. Always consider playing the pipe as a contrast or surprise or accent piece. That's when you can get away with the green stain or Oom-Paul, but you have to act as though you don't realize it's anything different, and only explain if asked, if then. It's a drama workshop.