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Strawberry Letter: I Want To Date My Sister’s Ex Boyfriend

Hi Steve, I have a problem that I need help with. I have been recently hanging out with some one who I known for 12 years now, we have a great friendship. Recently we have been flirting with each other and I really like him. I’m interested in taking our friendship to the next level. He does not know how I feel, but that’s not the problem. The problem is that he is my sister’s ex-boyfriend. They dated 12 years ago for about a year. She cheated on him which was the reason why they broke up. He has stood close with the family ever since. Now my sister has been married for the past 6 years and has kids with her husband. I really think that we would be very compatible together, but I don’t know how the family would react if we started dating. What should I do? Should I follow my feeling and tell him how I feel, or should I keep it to my self? I don’t even know how my family is going to react if we do start dating. We are very close as a family and I don’t want to stir up trouble . I also don’t want anyone to feel awkward because of me. Please help.

Signed

Alone and confused.

Listen to Steve Harvey respond to this letter below:

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