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Dating at Midlife/Midlife Dating Help: How to Handle the Holidays Together


My boyfriend and I have been dating since the beginning of May of this year. He lost his wife 2 years ago and has three children, 14, 16 and 19. I have my own baggage as my parents left my sister and I on our own when I was 15 and she was 13.
I met the kids very early on in the relationship. I am often at the house and participate in family things. He shares all family problems with me and I have gotten very involved.
We do not have sleep overs as he is not comfortable with me sleeping at his place.I have discussed many times that we then should have them elsewhere because that is very important to me.
As the holidays approach, we have been discussing what we will do over the holidays. I do not spend Christmas with my family and as such I always make plans to travel with friends or other nice things as the holidays are very important to me and many years ago, I promised myself to never have another bad one.
He is so happy to all the positive changes that I have brought into his life and family and would like me to help with all of the Christmas things but he is not comfortable with me sleeping there. I am not able to participate only partly. That really stings me too much because of all my family hurts from the past. I do not know how to get us past this.

Thank you for your help.

Hi Audrey,

Quick fine tuning question to you to help clarify things so I can best address what sounds like a midlife singles dating question.

How old are you each?

Are religious beliefs or any specific personal traumas for his kids holding him back from sleeping overnight with you? For example, did any of his 3 teenagers experience a severe trauma related to their mother's death?  

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April Braswell - Dating Expert


Can certainly address the romantic questions from Boomers looking to date again after divorce or the death of their spouse. Address how dating and courtship principles remain the same, however many of the tactics are different now. How to use social media and online dating sites well which reflect your age and style, not that of your grandchildren.


As seen in Dating for Dummies, 3rd edition. I'm an internationally recognized Dating and Relationship expert, frequently on Radio and serve as "In Touch Weekly"'s go to relationship expert for questions regarding celebrity couple relationships. Additionally recognized for specifically serving the different romantic needs of the Baby Boomer generation, having contributed to such media as Gateway Media, Woman's World, and The Boston Globe.

As seen in Dating for Dummies, 3rd edition.

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