Divorced Woman Wants to Know How to Start Dating Again

how to start dating again

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, 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 kids 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 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.


Katz and Stefani Family Law Attorneys


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 ended up 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.




2. 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. This is where I have to give you a little tough love and say, “then do something about it!”

I have no idea what you look like, but here are my suggestions on what you can do to make yourself feel more attractive (and keep in mind, I am making suggestions that don’t involve a lot of money because I know you are struggling financially.)

First, join a gym. If finances are tight, consider the YMCA or some other inexpensive facility. A treadmill is a treadmill and weights are weights. Who cares where you go, you’ll get the same result.  Another option: start jogging, biking or power walking outdoors. The weather’s getting nice, and your son could work out with you! That’s killing two birds with one stone: getting fit and setting an example for him. And, it won’t cost you a dime! I also recommend yoga. I swear by it!

Secondly, ask a friend to give you a makeover, someone whose looks you admire. She can help you with hairdo, makeup, skin care, and wardrobe. Just like asking someone for help 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.Plus, it will be fun. I have had friends come over and go through my closet, and we laugh and laugh about things they tell me to throw out and what looks good on me.

Lastly, the best way to feel good about yourself on the outside is to feel good about yourself on the inside. That means eating healthy, working out, being a good mom (which is sounds like you are), having fun and enjoying life, in general, enjoying your professional life, and making good, smart, ethical, selfless decisions.

So, are you inspired to start dating yet?

Let me leave you with one more piece of advice for getting back into the dating scene. The best 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 is the kick in the butt you need to jumpstart your social life. Just do it! Life is very short. It sounds like you love being a mom. Now it’s time to do a little living for yourself. You deserve that!

Buy novels by Jackie Pilossoph



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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. 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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