Strawberry Letter: Wisdom Doesn’t Come With Age

Dear Steve &  Shirley,

I have a boss that is looking for love but finds all the wrong men, especially young black men. She is white, but loves and has only 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 I’m still learning? 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, I guess because they are young and African American. I finally got her a date with my man’s brother. She gets her chance and within 24 hours of knowing him, she gives him some cookie in his car! Of course I am going to find out because that’s my man’s brother. I thought that she would have more class than that, since she is a successful, beautiful woman. The next day I had to go to work and act like I did not know and of course she didn’t tell me the details. Well, he never called her after she gave him some cookie and 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 and 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! She gave up the cookie and only knew the guy about 8 hours. I have tried to tell this woman in a nice way that if she wants to be in a relationship, she needs to move slow and let the man chase after her. I have been trying to avoid her, but I can’t 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 don’t even want to be bothered with her.