Dating Advice for High Maintenance Single Women

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Dear Sybersue;

I am in a very happy marriage with a man I love unconditionally! I love us together and want others to experience what I have too. I have a friend in Vancouver that is very depressed because she is still single at 40. She has never been married but turns her nose up at men she meets that have also never been married. (She thinks there is something wrong with them because of this! Hello, look in the mirror girlfriend!)

She also won’t date anyone over 40 or who have children. They also have to have a professional job with an income to match hers or better. She only goes to the best establishments & has a wardrobe that would make the Kardashians envious! She is beautiful which I think may be one of the problems with her expectations ~ she wants the trophy husband by her side to appear as the perfect couple.

When she does date, she makes comments on trivial things about men and won’t see them again because of the smallest reasons! I don’t understand how she became so stuck up but I know this is why she isn’t meeting someone. I have told her she is being negative and her “high Maintenance checklist” is ruining her chance of meeting a quality man. She just shrugs it off. She is becoming bitter and it is hard to be around her. I seem to be her only support and her family has never been there for her. What advice do you have for her?

Thank you, Concerned Shauna

Dear Shauna,

What a great friend you are for taking the time to write on her behalf. The message I get from what you wrote, is that she is “sabotaging” her own happiness by finding fault with each guy she meets. Many people do not feel they deserve to be in a loving relationship and judging by what you said about her family having never being there for her, this is probably the case. If you weren’t shown love as a child, it is hard to know what it is or how to bring it into your life. She sounds like she may be getting angry as the years go by because she hasn’t dealt with “this underlying issue.”

It is interesting how human nature works sometimes. The one thing we really want, we push away! It is all about self-esteem in the end. Sometimes beautiful women are very lonely due to the wrong attention they may have received in their life. There are some men who are shallow & just want the gorgeous girl on their arm without the relationship status. There are also the men who are afraid to approach beautiful women because they feel unworthy around them. Jealousy from family, friends and boyfriends can be a problem due to them feeling insecure in her presence. Some of these situations over the years may have jaded her or she just may have always had a “sense of entitlement” built into her personality due to her given beauty. Whatever the case, it’s not working for her!

Her tough exterior is really an insecurity that she is making an excuse for. The fact that she discusses being single all the time with you, shows that it is a concern for her and she really does want someone in her life. (This seems to be a constant topic with dating in Vancouver!) I would advise your friend to seek some counseling very soon or she will not only remain single, but also lose you and other friends who are tired of her pessimistic attitude.

She is not doing herself any favors holding onto this princess behavior and men in their 40’s have little time for it. Pretty soon she won’t have to worry about being too picky with her men because there won’t be any men to pick from. It’s never too late to make changes in your life and become a better person. The one thing we all have in common & need in our lives is; love. It is the universal language that we can all relate to and need to exist. Why would we choose to repel it?

Dear Sybersue @


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