For almost a year now, I have gotten back in touch with a old friend from high school whom I had a crush on. Little to my knowledge, she actually had a crush on me as well. As much as I want to ask her out, I measure her career success next to mine. I'm nowhere close to her status at the moment, even though it doesn't take away from anything else I have done with my life. With such a wide gap in our economic and social status, should I still go for it?