Does Midlife Dating Make You Terrified? Actually You’re Not Alone

September 16, 2016

Dear Mrs R Does Midlife Dating Make You Terrified? Actually You're Not Alone

Dear Mrs. R – An Advice Series for Women of All Ages

I am so excited to bring you another installment of Dear Mrs. R. I truly value all of my readers and your support has been amazing. Thank you from the bottom of my heart!

In an effort to protect my readers privacy, I will refer to only a First Name and Last Initial when posting to Dear Mrs. R. So, please do not worry about your confidentiality as it will be protected. That’s my promise to you! Also, I will not publish any question without the express permission of my readers.

This week I chose a question from Vanessa B. Vanessa asks:

Dear Mrs. R, I feel a little silly coming to you with this question but I really would like your insight. I’m a 56 year old widow. I lost my husband 12 years ago to cancer. The loss of my husband traumatized me for many of those years. So between the grief I was experiencing, going through menopause and trying to hold it all together for the sake of my children I ended up gaining over 78 pounds. I was one who dealt with things through food. The weight gain caused some health problems and my doctor said that I needed to lose the weight if I wanted to have any kind of quality of life. At the time I was 250 pounds. I was worried about not being here for my children and grandchildren so I went on Weight Watchers and started exercising at the community center. I was determined to lose this weight. I’m now proud to say that I have lost 107 pounds!! My children can’t believe it and neither can my friends.

But, that’s not why I came to you. I feel wonderful and am really proud of the way I look so I’ve been getting out a lot more with friends. You know, dinner, coffee, movies. I’m having a wonderful time! Well, until I was asked out on my first date! At first, I didn’t think he was serious so I gracefully declined. I keep running into him since he’s a good friend of my friend’s husband. I never thought in a million years I would ever be dating. But, now my friends are nudging me to get out there. Mrs. R, I’m terrified!  I really never dated when I was young. I married my late husband when I was 18. He was my first and only. I often think that it would be nice to have someone to do things with. I do feel lonely at times and I’m afraid of being alone for the rest of my life. But, I’m terrified!!!! What do you think about dating at my age? I look forward to hearing from you.

Vanessa gave me a good chuckle with this one lol. I’m certainly not an expert in the dating arena! I haven’t dated in 20 years!! But, I always like a good challenge and feel this question resonates with quite a few of my readers so I’m going to give it a go!

Dear Mrs R Does Midlife Dating Make You Terrified? Actually You're Not Alone

Dear Vanessa:

I have been married for 20 years so I certainly can’t call myself an expert in the dating game but I will do my best, okay?!

I want to give you a huge round of applause for losing 107 pounds!! I think that is awesome!! You should feel very proud about your accomplishment. Now, to address your question.

I can understand how dating at 56 would be terrifying. But, I don’t think your late husband would want you to live the rest of your life alone. I’m sure he would want you to find happiness and love.

It does seem that you have crossed the grief threshold and have started to move forward with confidence. So, I would start by pondering the questions, “Why do I want to start dating?” , “Can I date without feeling disloyal to my late husband?” and “Am I dating in search of a replacement?” I think the answers to these questions are very important. First off, if you desire to start a new chapter in your life then I think it’s perfectly understandable to want to share that new beginning with a companion.

However, if you feel you would be dating in an effort to replace your late husband I feel you will end up disappointed. You will never be able to replace him or the love and life that you shared together. But that doesn’t mean that you will never find love again. The love you and your late husband shared is a special kind of love that can never be replaced. You will cherish that love and store it securely in your heart and soul forever.

Now let’s take a look at feeling disloyal. You may feel confident now that your late husband would want you to move on but it won’t be until you actually go on a date that you will have your answer. That first date could spark the feeling of disloyalty. If you go into it knowing that feeling may come up, recognize it for what it is, feel it, but don’t let it hinder the experience. You are just spending time with someone who hopefully shares the same interests and passions as yourself. Dating, simply put, is a potential for connection. The key here is to relax and enjoy the process.

With that said, instead of meeting your first date at Starbucks why don’t you suggest meeting at the zoo, a park or a museum. It will ease the face to face jitters and can be a fun way to get to know each other. You will have many things to talk about without feeling you must keep the conversation flowing. If things do not point to a second date at least you had an enjoyable day out and possibly made a new friend.

Once you get past that first date, I’m certain you will feel more confident about the next. Vanessa, the key is to get out there and have fun during this new chapter of your life. You deserve it!

If you enjoyed this installment of Dear Mrs. R than you may enjoy Dear Mrs. R – Weight Gain & Breakouts? 3 Amazingly Valuable Tips to Know and Dear Mrs. R – 5 Valuable Steps to a Healthier Clean Home. It’s Actually Easy!

If you have a question you would like me to address, please send an email to I will do my very best to give you a well researched answer and hopefully together we can come up with a solution. There are no questions too big or too small!

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See you in the comments,

Simplify Life With Mrs R


By Mrs. R