Dating After Divorce: My First Date In 20 Years

36 years old and have never been on a date.

I stood in front of the mirror very nervous. I had so many questions. Would he look like he should? Would we find something to talk about? Who pays the bill? Did I look too desperate? Too tarty? Too modest?

There was no turning back now. Time to go. And the rest, as they say, is history.

Dating After Divorce: Happy couple

My Past Relationship

My past relationship was with a high school sweetheart. We started dating at 16, were married at 21 and after 20 years we went our separate ways.

As you can imagine there wasn’t a lot of dating at 16, more just stolen kisses on the school grounds. I remember always thanking God I never had to do any of that “dating stuff”. It seemed like hard work.

20 Years Later

When my relationship fell apart I felt old. Twenty years with someone can do that to you. Plus three years of family law court sorting out child support and assets.

But after a serious bout of depression during my horrendous divorce, I started to notice that most people my age hadn’t even been married yet.

I wasn’t old. I was experienced.

Little did I know in the city I was visiting there was a divorced man who had experienced the same situation. A failed 20-year relationship and newly single, finding the dating scene full of self-absorbed females, and multiple disasters.


Dating Apps

On a vacation in Perth, I met a friend who introduced me to dating apps. I was mortified but assured that this was 2017 and this is how people did it. So on I hopped for a bit of fun and a flirt, which I hadn’t done since 1997.

There are so many dating apps to choose from, it can be hard to know where to start. I’ve had so many friends successful on one, or not successful on the other. Some seem just to be for hookups, whereas some are designed for a lifelong commitment. I wanted neither.

dating after divorce - girl on computer

A Decision

After talking to a few guys, there was one that I kept getting drawn back to. After two weeks of daily chats, I rang my experienced friend in Perth and told her all about him and said, “I think I want to meet this one.”

It brought up so many emotions. I felt fear of failure after the first one had ended. I felt guilt, despite being a divorced person it felt like cheating, and I’d never looked at another guy that way in twenty years.

Lastly, I felt excited. What was a first kiss like? It had been so long, I couldn’t remember. What did it feel like to flirt and touch and …. I’m sure you understand.

Dating after divorce

The Outfit

Having lost some 25 kilos in the last 6 months I had nothing to wear. After my divorce, I was a new person. I’ll never forget the staff at Forever New at Highpoint Shopping Centre. I explained I was going on my first date and the staff pulled out all sorts of dresses, tops, and pants for me.

I felt good. I was ready.

Check out some date night outfit ideas here.

dating after divorce - smile divorced girl

What’s the best first date?

I’ll never forget the story of a girlfriend whose first date was on the Melbourne Star. A large Ferris wheel much like those found in several countries. It was so horrible and she was stuck on that hour’s journey with no escape.

So, activities for a first date seemed like a no. At the same time, I felt dinner was too much of a commitment as well. A simple drink seemed like the answer. I don’t drink coffee so an 8 pm cocktail was my plan.

dating after divorce - happy couple

Was I Catfished?

That night I met a girl friend for dinner to try and enjoy myself and calm my nerves before I waded into the dating pool. She walked me to the meeting spot and I texted I had arrived.

Turns out he knew a thing or two about online dating and had already arrived to scope out the situation. I don’t know what type of people go about catfishing, but he decided with one look he hadn’t been and came to meet me at the door.

And I was definitely not catfished. Hubba hubba! He was hotter in person.

dating after divorce - hot man

Who Paid The Bill?

This was easily solved when he asked to buy me a drink before we sat down. Once the lady asked for cash, he said he only had his credit card. They didn’t accept any type of card.

Now I get that is absolutely crazy, and thankfully I had cash so guess who bought the drinks that night?

I’ve never let him live it down.

dating after divorce

How Did It Go?

We spoke for hours over just one drink. He was charming and funny, very forward, and very cocky. But I loved it. I got to be completely feminine and he led the entire night.


Having never dated like this in my entire life I had no idea what he was thinking and feeling.

Not until the next day.


What Happened Next?

At the end of the date, he said he’d call me the next day.

I was dubious.

But he did. I admitted my surprise to him and I’ve never ever forgotten his words, “Why are you surprised? I enjoyed my time with you and I was hoping to see you again.”

Call me gobsmacked. Maybe my self-esteem had taken a beating from my divorce, maybe I was terrible at reading men, maybe I was protecting my heart, maybe it was all those things.

But after hearing those words we had a movie date planned 3 days later.


It’s been nearly 6 years since that first date with Ahmet. At 42 I’ve only ever had 2 relationships in my life. Some call me lucky, some call me crazy.

I am not a relationship expert, but from what I’ve learned during my post-divorce relationship here are my top tips for getting back into dating after divorce.

Tips for Dating After Divorce

Grieve your loss

Whether it was your idea or their infidelity or any other number of things that ended your marriage divorce leaves you shattered. Say goodbye to all those things you thought you lost, like in my 10 Lies Divorced Mums Tell Themselves. Recognize the things that are truths.

No one can tell you what length of time this will take you. Only you can do that. And maybe you won’t ever be ready and just need to jump. Maybe you’re ready faster than you thought.

A therapist is a great way to accurately identify where you are at in your healing and determine when you’re ready to start a future relationship.

dating after divorce - happy couple

Recognize the things that went wrong in your marriage

You know it takes two to tango. So whether it’s admitting you were a really bad judge of character just to start with or if you were the reason for your divorce, recognize the mistakes and faults. Own them. And move on from them. Only this way can you not be doomed to carry out the mistakes of the past.

Identify what you want in a new spouse

After 24 hours a day, 7 days a week for 5 years with my last partner in nomadic travel I wanted a man that went to work and came home. One I could miss and love being around, rather than resent. Write yourself a list and use your list as a guideline on what is a possible match for your new relationship.

dating after divorce - happy couple

Be safe

We all get caught up in the romance and mystery, but please ensure someone knows where you are! Other than my friend with who I had dinner, I also had a mate in Melbourne whom I had texted to tell him where I was and what my plans were.

Even if you are a good judge of character in public, don’t be neglectful of your own safety, no matter how embarrassing.

Take it slow

Two weeks of chatting. I was not in a rush to meet just anyone. Since that first date, our courtship has been long and purposeful.

We have spent many conversations getting to know each other. Traveled alone, traveled with kids, fought about big things and small things, and discussed religion, marriage, and children.

I’d have to be surprised if after 6 years we didn’t know each other, but I’m in no rush. After all don’t we have a lifetime to build a healthy relationship?

dating after divorce - kissing couple

Don’t rush introductions

It took a full 9 months before I even introduced my new partner to my children. After the trauma of multiple girlfriends, their Dad had put them through I knew they wouldn’t get that from me.

I wanted to introduce them only to a man who would be in their life long term and that took many discussions before I thought that might be the case.

Their first meeting was a quick lunch at KFC. The second was a BBQ with friends where he ran a soccer game with all the kids…. I was in love!

Child Care

When and how you have your children plays a huge part in dating after divorce. I was thankful my kid’s dad was around during that year of dating so I only dated every second week when they were at their dad’s and then a bit more regularly with the help of my parents.

If you do not have someone to watch the kids it can be so much more tricky, which is why many women end up single for long periods. Not out of a lack of interest, but out of a mother-bear attitude to their children and a commitment to family life.

Dating after divorce - hanging from a tree

Be Ready To Date

When I look back I am not sure I was ready. But I don’t know what it would feel like to be ready. I’m no expert in the divorced woman field.

I feel like dating sped up the process and intensified all the emotions. I never expected to find my next committed long-term relationship that fast, but I wouldn’t change it for the world.


Forget whatever you think your type is

At 15 I was sold on blue eyes and blonde surfer hair, as my daughter recently read in a bunch of letters I wrote to her at that age. And here I am with a swarthy dark-haired, dark-eyed Zeus. Forget your type.

Don’t be afraid to talk about finances

After the trauma of losing Travel With Bender and a substantial amount of money in my past marriage, this was an early conversation for us. We made a Financial Agreement when we bought a house and made promises never to make the mistake of a costly divorce no matter what.

dating after divorce - kissing couple in bali

Top Questions Asked By Women After Divorce

Top questions most divorced women ask themselves when looking to date after divorce.

How long should you wait to date after divorce?

There is no magical timeline and multiple articles will give you multiple results. For me, it was the finalization of a long-term failing marriage, and after multiple sessions with a great psychologist.

Does the first relationship last after the divorce?

Statistics show that the first relationship after divorce usually does not last long. If you haven’t found someone you can work through your emotional baggage with or overcome the insecurities from the last one, it won’t work. Guess I got lucky.

dating after divorce - kissing couple

What percentage of couples get back together after divorce?

Research suggests that 10-15% of couples reconcile after they separate, and about 6% of couples marry each other again after they divorce. That is not a high percentage and in my opinion, not something to be scared of when you get into a new relationship.

What to look out for when dating a divorced man?

Make sure he’s actually divorced. Recognize his ex-wife will be part of your life and ask yourself if you are okay with that. Understand he may struggle with the idea of marriage again.

dating after divorce - romantic man

Dating Favourites

Couples Bucket List Ideas

Boundaries in dating book

Date ideas scratch poster


I’d love to hear successful stories from women who have dated after divorce. If you’re okay sharing below, even anonymously please give me your best tips for dating after divorce.

Also read Yes, I’m a Christian Dating A Muslim!




FOMO - do you have it?  Well there is no need to Fear On Missing Out here at Explore With Erin. Sign up to receive updates directly to your in box. I won’t spam you, but I do promise a whole lot of awesomeness. What are you waiting for? Join Me!

PS: We hate spam too, read our Privacy Policy here.

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Start typing and press Enter to search