<prompt> Human: 35F. No debt or student loans. My personal finance plan is in check. I work at a male-dominated brokerage firm and Im primarily commission-based. Heres my dilemma. I have a big client Ive been chasing for awhile. We go to lunch about once a a quarter and Ive developed a solid relationship with him. His portfolio and his is with another firm. I think I can land him as a full time client if I spend thousands of dollars on entertaining him at the super bowl in 2019 since itll be in my city. Im working with a company to find out exactly how much this would all cost but I think it would be about 8k for a nice experience. My firm does not shell out money for client entertainment. So this would come out of my pocket. He has not indicated that he is willing to give me his business but I think this would move things further along since he loves football. Im just struggling with taking a gamble on spending so much money on someone who isnt even my client. What would yall do? Thanks for reading!  <response>: Dont do it. 