Dating at Midlife/Shy Yet


QUESTION: Hello Lauren
         I am a single male of 61 thin built and average height.  I have lost hair on top and wear glasses. But am nice looking.  And and nice person.  But still on the shy side.
I turn red a lot when a women  just talks to me.   I never ,married  never really got close to even having a girl I COULD CALL A GIRLFRIED  jUST SORT OF FRIENDS.   I only had sex twice and both times the girls had me on bottom. Because of my shy ways  I did sort of like a women who works at  my dentist last  month she is a few months older then me she seems nice but I COULD TELL WHAT SHE WAS LIKE   SORT OF WILD AND SEX  I FELT VERY SHY AROUND HER AFTER A HOUR.   Is there any hope for me?   Also I would like a girl taller then me  and who likes wearing skirts and dresses makeup  most the time.   Do women like shy men?   Can they tell I am shy when I get red in face just talking to me   

ANSWER: Hello, It's hard to imagine that a man of 61 had sexual relations twice.

"  I only had sex twice and both times the girls had me on bottom".

I think you're not giving this a chance to know what you want or like. What is your personality telling you?. Are you happier with shyer women or more seductive women. You risk less with more seductive women knowing that they will dominate you. I think reading up on attraction, attracting the right type of person for you will help you in determining future relationships.

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QUESTION: Hello  Lauren
         Thanks for answering my questions
    But why is it hard for you to imagine I ONLY HAD SEX TWICE?
 Is it all that bad?    I know sex is part of dating today but I only THINK BOTH NEED TO CARE A LOT FOR EACH OTHER NOT JUST A FRIEND.  Plus you have to be very careful today.  I know I AM SHY AND thats why they both talked me into it.     Its true I think I  LIKE a women who is a little seductive  and taller. Because of my shyness. However   I would also like a shy women too.  But where are they?     I love taking nature pictures and have  many cameras and lenses for them   I also don't drink or smoke and love dogs.. and work hard . hope there is some one for me


Hi Johnny, it's hard for me to imagine because...... most men your age has had meaningful sexual relations at least twice. The fact that you had sex twice with woman who "lured" you is not careful, not caring and I think if either one of those relationships were meaningful, you would still be with one of them. I love the fact that you have interests. That's a wonderful place to start. I don't know where you live, but there's a wonderful organization called meetup.

Here's the link:

This organization based on your zip code will find groups of people that have the same interest as you. It's primarily for you to meet like minded people. In that venue you might find someone similar where you can forge a meaningful relationship. Good luck and let me know how it went.

Dating at Midlife

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Lauren Stevens


I can answer all questions pertaining to dating, dating at 50+, online dating, health and sexual issues regarding relationships.


I have been a life coach and all expert coach for over 15 years.

I have founded and facilitated Life After Divorce a coaching program that promotes and enables life changing events. I also facilitated Transitions a support group for the traumatic experience of people going through divorce and the newly divorced.

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