You are the best litmus test you have for other people. Don't hide yourself from others when you first meet them for fear of scaring them off. Chances are, if they aren't ok with the reality of who you are the first time around, they aren't going to get any more comfortable as time marches on. I never liked the idea of personality of something that needs to be leaked out in small doses as if you were trying to slowly poison the other person with it. The big fear is that by putting yourself out there up front, you can get yourself hurt. The truth of the matter is that the less time you take to get things out in the open, the less you'll have invested if its all too much for the other person to take. That saves you getting hurt more than anything else. Your experiences, sketchy or otherwise, are who you are and not to be apologized for. Make no excuses for what got yourself to this moment. Perhaps if we were all so comfortable with ourselves in the first place, we wouldn't do have the regrettable things that make opening up so uncomfortable. I hate "excuse me" personalities. I wish more people were "take me or leave me." I can respect that immensely.
I invest in seed and pre-seed NYC startups at Brooklyn Bridge Ventures. Native Brooklynite, 14x triathlete, 4x 70.3, 4x marathoner, softball player, hockey goalie. Check out my This Week in Startups interview or check out my bio here. Also, this is me SEOing myself by linking to Charlie O'Donnell, and Charlie O'Donnell and more Charlie O'Donnell. PR people, do not pitch me to cover your story, as this is my personal blog. I'm not a journalist.