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Strawberry Letter: 50 And Hot To Trot

Dear Steve & Shirley,

I have a boss that is looking for love but finds them in all the wrong men especially black young men. She is white but loves and only has been with black men. She’s about 50 years old and needs to work on her self esteem. She confides in me about finding the right one but how can I tell her how to find a man when I am half her age and am learning myself.

She has been asking me to help her out with finding a man but the only ones she seems to want to date are my man’s friends. Why I guess because they are young and African American. I finally got her a date with my man’s brother who she was interested in because I have a picture of him on my desk. Finally she gets her chance, now within less than 24 hours of knowing him she gives him some cookie in his car!

Of course I am going to find out b/c that’s my man’s brother! I thought that she would have more class than that being that she is a white successful beautiful woman. The next day I had to go to work and act like I did not know. Of course she didn’t tell me the details. Then he never called her after she gave him some cookie. Now, she is depressed and asking me tons of questions about his whereabouts. The bad part is that he told her before they went out that he was involved with someone else. I told her too but she insisted.

Now, six months has gone by. She is over him. Recently, we went out after work and invited my man and his friend and she did the unbelievable she did it again! Gave up the cookie and only knew him about 8 hours. I have tried to tell this woman in a nice way that if she wants to be in a relationship that she needs to move slow and let the man chase after her. I have been trying to avoid her but I cannot because she is my boss .

Please help me. What should I do because here she goes again getting depressed and I am to the point where I do not even want to be bothered with her.

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