If I were dating, I would put all my “baggage” in my description on my dating site of choice. Then the people who didn’t like it would self select out, and I’d never have to deal with them. The people who were interested would know up front and it wouldn’t ever be an issue.
For dating in person… well, this is why I have never done that and never will. Dating is not a good way to get to know people. I get to know people doing other activities, and by the time we start getting romantically involved, they already know a lot about me just from talking to me and others in non-romantic situations.
Dating is so artificial and prone to gamesmanship. I don’t even know how people get to know each other, unless they are really pretty bland people and there’s not much to know. But if you have differences, and you are always worrying about how to present them or whether to present them and when to present them—how can you be natural? How can you be yourself?
When I was a teen, I thought I had to pretend to be someone else in order to impress a woman. Money, brawn, being impressive—that what I thought you needed to be successful at dating. I wasn’t impressive. Not by a long shot. So I never dated.
But that turned out to be a good thing. A few women actually liked me when they got to know me in a natural way. I may not be impressive, but that doesn’t mean there’s nothing to like. Later on, I even discovered that showing your flaws can be attractive. There are women who like men who aren’t anywhere near perfect. I’ve even been accused of being interesting.
So I don’t think dating is really a good thing to do, and if you have baggage, whatever that is, it’s probably a really unfortunate way to meet people.
Be flawed! Don’t date! ;-)
Hmmm, I wonder if you could set up a non-dating dating site on this principle. J-don’t-date!