In a related question, how what is the best way to bring my less than steller current circumstances up? I'm on a dating site right now, and in my profile, for obvious reasons, I highlight my strengths. Their is a girl there who I haven't chatted with much, but it sounds like she is someone I'd like to meet and also sounds like she would be up for coffee sometime soon. She's also a year older than me and more successful. I hesitate to tell her of my current situation through a message because then she might not want to meet. But it would also be awkward to bring it up while we hang out (but at least then, she would have the opportunity to get to know me first). Any advice?
I think that if she's going to be put-off by your current situation, then she probably will be whether you tell her up front or you tell her later.
I think that your best bet is to go ahead and tell her where you currently are in life but do it in a positive way. Not telling her up front could have the unfortunate side-effect of making her think you're hiding stuff. (What else did he not tell me?)
The way you word it here (calling your current status relatively unsuccessful, for example) betrays that you are a bit insecure about it. Be careful not to poison your own well.
Turn the negatives into positives:
"I still live with my parents" becomes "My parents and I have a great relationship, living with them to help us all share expenses is good. I'll eventually leave them on their own, but right now this works best for all of us."
"I don't have a steady income" becomes "I'm getting my feet under me, learning how to implement the skills I learned or honed in school. In the next year or two, I'll be walking stronger and stronger."
"I haven't graduated from college yet" becomes "I'm a week away from having earned my degree and I feel great about what I've accomplished."
It may seem like PR spin... but people view us the way we present ourselves. If you show by your words that you are confident in your abilities, confident that you will one day soon be earning a steady income and self-sufficient, then others will also have confidence that you will do those things. (Also, if you have confidence that you can do it, you're more likely to do it).
I hope this gal is cool. If she doesn't like you for where you're at in life right now, then she's not cool. You are successful and you will continue to be successful. You've got the drive to get it done, where lots and lots of people have already quit. Any woman worth her salt will see that.