I like one of my Best Friends ex-boyfriends, what should I do?


October 7, 1964, Wednesday. Went crazy and called Jack… World Series starts today.

It’s getting better everyday. Kid’s at school are even taking bets to see how long I can last wearing this black wig. People are getting used to me as a brunette. All we did was talk about Dave and Jack and old times today. After school I went shopping to buy my sister Donna and her friend Linda K. their Pledge stuff. Tonight for some reason I actually called a boy. I wanted to get Bill’s number for Sandy, so I called Jack. He was so nice. We talked for a long time. He hasn’t changed a bit. He even told some dumb jokes. He really sounded happy to hear from me. I sorta broke the ice. I think I could really like Jack, but I couldn’t hurt Sandy. I called her later and she almost passed out when I told her I called Jack. She likes him so much. That’s why I will never go out with him.


saffrons rule talking on the phone with a guy

  • I Like My Friend’s Ex-Boyfriend

    I want to date my friend’s ex what should I do…

    Dear Dr. G.,

    I am a 17-year-old girl and I’m going into my senior year of high school. I have a serious problem. At least it’s a problem to me. Maybe other girls wouldn’t think it’s a dilemma but to me it is.

    My friend broke up with her boyfriend of 6 months about a month ago. I’m working at a day camp this summer with guess who? my friend’s ex-boyfriend. My friend liked this boy a lot. I’m not really sure why he broke up with her. She didn’t talk about it much but she seemed upset when it happened. Now that I’m working with this boy-maybe we can call him Jim-I’m starting to like him. I am pretty sure that he has feelings for me too. He asked me to go to a movie this past weekend but I said no because I was so nervous and confused about what to do.

    Dr. G.:Are there rules about a situation like this? I would like to go on a date with Jim but I don’t want to upset my friend and I don’t want other girls to get mad at me. Do you have any advice? I asked my mother and she said that I should write to you. So, I listened to my mom. HELP.

    A Confused Teenage Girl

    Dear Teen,

    You are struggling with a dilemma that women,men,teens and adults deal with throughout life. There is, of course, no simple answer to your question about when and whether or not it is socially acceptable to date a friend’s ex. There are no clear social rules about this but we can try to tease things apart and discuss some unwritten social rules and etiquette.

    1. First, how recent is the break-up?

    If your friend and this young man broke up within the past week or so then I would suggest that it is too soon to start dating her ex-boyfriend. After a month has passed I believe that you can consider dating him. This allows your friend some time to move on.

    2. Second, how close a friendship do you have with this young woman?

    If she is a close friend then I would suggest that you talk to her and let her know that you are considering dating her ex-boyfriend. Clearly, she does not own him but you do want to be both a sensitive and kind friend. In my experience, friends appreciate hearing directly from friends rather than learning sensitive information from others. If she is not a close friend then you do not need to discuss your dating plans with her. You also do not need to talk about her ex around her regardless of how close you are or aren’t. Sensitivity is always a virtue.

    3. Third, how upset is your friend about the break-up?

    If you have a close friend who is reeling from a break-up then you absolutely need to speak to her and talk to her about her feelings about you possibly dating her ex. If you have made a definite decision to date him then let her know that and reassure her that you will date him but will be low key about it

    You may also want to find out what went wrong. She may share information that is important for you to know regarding this young man.

    If your friend is not terribly upset about the break-up and has already moved on and re-grouped then the coast is clear for you to date the ex.

    The answer to your question is that YES you may date the ex but do so with sensitivity and after an appropriate amount of time has passed. In life, we meet and start to fall for people who we are familiar with and that includes the ex-boyfriends and ex-girlfriends of friends

    It is a shame that things aren’t simpler but in life all things related to relationships and feelings are complicated. Go ahead and get to know this young man. I hope that you are also able to maintain your friendship with your female friend.

    Good luck and let me know how the summer goes.

    Dr. G

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About saffronsrule

Sharrie Williams is the author of The Maybelline Story and a direct descendant of the Maybelline Cosmetic Family. Great niece of Maybelline founder Tom Lyle Williams. Buy a signed copy today.
This entry was posted in 1960's Surf Culture, 1964 High School Diary, Chick Secrets, diary, Little Sisters, Maybelline Girl, memoir, REALITY BLOG, Southern California 1964, teenage reality blog and tagged , , , , , , , , , , , , , , . Bookmark the permalink.

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