Divorced Woman Wants to Know How to Start Dating Again

how to start dating again

By Jackie Pilossoph, Creator and Editor-in-chief, Divorced Girl Smiling site, podcast and app, Love Essentially columnist and author

Divorced Girl Smiling received this comment from a woman seeking inspiration and asking how to start dating again.

Still kind of saddened by my divorce of 6 years ago. My ex’s son and I live across the country and enjoy a new life – but with single mom duty and a very, very thin budget, I just do not understand how dating is even doable. 

 Babysitters cost more than I have, plus all my time goes to being a mom anyway. How on earth do most find the support/money/time to date?? How does one help with homework, make supper, clean up and date all at once??

 I envision dating again when my now 11 year old is in HS, I guess. But with mom duties now, I cannot see it happening. I wonder how other moms of children do it. Maybe it’s age-related too. I’m 51 and not feeling so hot about my looks these days either. Feedback, anyone? How in hell would I start?? Someone, inspire me on how to start dating again please!


I was sad reading your comment, but hopeful, because I truly think, like you said, you just need to be inspired. I have a few ideas for you about how to start dating again.


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First of all, do you realize how NOT alone you are? Every single parent struggles with balance when it comes to raising their children and trying to have a social life and/or date. Here are three obstacles that prevent men and women from dating after divorce:

1. Guilt:

Many single parents feel guilty getting a babysitter to go on a date (even if money isn’t an issue) because they feel they are doing something wrong by leaving their children home, when the children are dealing with the divorce.

I can’t tell you how wrong I think it is to feel guilty!! Let that go! Just because you are divorced, doesn’t mean you don’t have the right to enjoy your life. You aren’t doing anything wrong!

2. Money:

Single parents might not date because they feel guilty spending money on a babysitter if finances are tight, or they simply can’t afford the sitter. Possible alternatives to getting a sitter are to bring the child to a friend’s house while you go on a date. Do you know how many people would welcome the opportunity to help you in that regard?

Don’t be afraid to tell the parents of your child’s friends your situation. I can assure you they will be more than happy to help you out. Another alternative is to meet your dates for lunch on your lunch hour at work (while your child is in camp or school.) Lastly, there are lots of high school kids who charge so little for babysitting. Your son is 11. He’s almost old enough to stay home alone, so  a high school babysitter is probably a safe bet.


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3. Fear: 

Everyone is scared sh**less  to date after divorce, yet there is an excitement we all feel, too. At some point, it’s like getting up the guts to just get on the roller coaster when you were a kid. You just have to do it. You’ll be glad you did!

Next, I’d like to address your comment about being 51 and not feeling so good about your looks. Being a woman in my 50s, I can relate. What I’ve learned are a few things. Aging and physical changes are inevitable, so stop stressing about them and work with what you have. What do I mean by that?

Control what you can, and love yourself for who you are.

For example, if you dont like the wrinkles on your forehead, get Botox. Now, that might sound superficial to some people, but I think that when you get cosmetic procedures like that, it makes people feel better about themselves on the inside, so they exude more self confidence and are happier. That said, be very careful. I know some women who are addicted to plastic surgery. Try to remember that doing little things is great, but what matters so much more is what you bring to the table from the inside.

I promise you, you will find that men really care a lot more about personality than perfection. And trust me, they’re not physically perfect either!! So, if you can get to a place where you are happen”enough” with your physical appearance, and you feel HEALTHY emotionally and physically, that’s more important than comparing yourself to others, and/or trying to look like you did 10 years ago.

A very important aspect is feeling healthy physically and emotionally, which translates into making sure you are exercising both your body and your brain.  This includes:

Lifting weights

Cardiovascular workouts




Reading/puzzles/writing: to stimulate your mind

It sounds overwhelming, but you have to do it all! Not all every day, but mix it up. You have to do a few of these every single day. Studies back this up. But try to find fun ways to do these things! A nature walk with your kids, a 30 minute cardio class on YouTube, reading a book a month, etc.



Other ways to feel better about yourself are to let professionals help you. We aren’t stylists or makeup artists, or health coaches. But they have made their services very affordable to people. Here are some examples of things I love:

StitchFix Which basically sends stylish clothing to your home and you can try them on and return anything you don’t want. It’s very personalized!

Daily Harvest They have incredibly healthy smoothies and oat bowls and veggie bowls and pizzas that will help you nourish your body and feel so good!

The Mirror I’ve been doing workouts on this for 6 months and I LOVE it!! It feels like you are at a gym.

Take Supplements. Ask a functional medicine physician, a chiropractor or a health coach. I swear by these!! You can take natural herbs that help for anything! The ones that have helped me are for: sleep, back pain and arthritis.

Therapy. I truly believe in therapy for every person getting divorced and after.

Other tips: when it comes to babysitting, don’t be afraid to seek help from someone in this regard. I think the person will be more than happy to help, and will actually be flattered.

Lastly, the best way to feel good about yourself on the outside is to feel good about yourself on the inside by doin the following: recognizing what a good parent and good person you are. Go easy on yourself. You’ve been through a lot and you are doing the best you can. You aren’t perfect. No one is. It’s OK to make mistakes. It’s human.

Also, follow your passion. Do things you love. What did you like to do before you got married and had kids? What were you good at? Go do that!! (or something similar). If you loved basketball, maybe you can be a volunteer coach. If you loved art, maybe you can go work in that industry. When you love what you do, you are happier, oh and did I mention it’s the best way to meet someone?

So, are you inspired to start dating again yet?

Let me leave you with one more piece of advice for getting back into the dating scene. Another great way to meet men is to ask your friends, co workers and people in your community if they know any single men for you. In other words, network. And again, let your community help you! So many people get joy and satisfaction out of helping others! I know I do.

It’s hard to ask for help, and it’s hard being a single mom with no alone time and financial stress. I get it. I really do. None of my advice for dating is easy. I know that. But this might be the kick  you need to jumpstart your social life. Just do it! It sounds like you love being a mom. Now it’s time to do a little living for yourself. You deserve that!

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    Editor-in-chief: Jackie Pilossoph

    Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

    One Response to “Divorced Woman Wants to Know How to Start Dating Again”

    1. Lisa

      I noticed you didn’t mention joining a dating site. I too am scared as hell to start dating again. I joined a site and just couldn’t seem to get up the nerve to actually meet someone. There was a real disconnect between the guys who were interested in me and those I was interested in so I cancelled before actually going on a date. Any suggestions?


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