How to Date After Divorce at 40: 11 Tips

how to date after divorce at 40

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

As someone who dated from the time I was 16 until I got married at 35, and then dated again at 41 until I was 49, I have a lot to say on the subject of dating, both before and after divorce. In many ways, dating as a teenager isn’t much different than dating in your 40s. The basic rules, feelings, and experiences have many similarities. But how to date after divorce at 40 comes with some challenges:

1. You might have children and you might be nervous about them finding out or how they will react to you dating.
2. You’ve aged. (Although I think people get better looking in their forties.)
3. You might have some health issues.
4. You’re more experienced, yet you might possibly be feeling apprehensive and scared because you haven’t dated for so long.
5. You might feel more vulnerable, maybe more insecure, especially if your spouse left you.
6. You might be cautious and having a hard time trusting anyone because of your former spouse and/or marital experience.
7. You might still be mourning the end of your marriage or have hope that it is going to somehow work out.
8. You might feel pressure to get married again, which is coming from friends, family members or yourself.
9. You might be trying to juggle being a single parent, working, and dating.


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Despite all these things, I can speak from experience that dating after divorce at 40 has its advantages, and can be extremely fun, fulfilling and meaningful.

Here are 11 dating tips for how to date after divorce at 40:

1. Stop looking at your phone.

If you have children who might need to reach you, I’ll give you a pass. But other than that, you need to be engaged in the evening. I am constantly seeing people using their phone as a crutch–as something to do when they feel subconscious. Stop. Just stop! It’s a turnoff. When you are out, try putting your phone in your purse or your pocket and not looking at it. This way, people will notice your whole head, not just the top of it!!

2. Smile and be approachable.

When a bunch of women go out for a girl’s night, they don’t realize that a large group can be intimidating and overwhelming to men. So, if you see a guy checking out your group, smile at him. Let him know it’s OK to come over and say “hi.” Or, what’s wrong with YOU walking up to him and starting a conversation? Nothing!

3. Compliment her.

Compliment a woman’s shoes or her purse or her smile. Try to stay away from commenting on her dress or her body. Women can be very sensitive to those kinds of comments.


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4. Being Direct works.

“Hi, my name is Joe, may I buy you a drink?” Simple and honest. No games.

5. Try some humor.

Let’s say you’re in a really long line at Starbucks and there’s a cute guy in front of you. Say something funny about the line. Be friendly and witty. You have nothing to lose!

6. Be a wingman for your friend.

There’s nothing wrong with walking up to a girl and asking, “Are you single? I think you should meet my friend.” Even if the person isn’t single, he or she will take this as a compliment and appreciate it.

7. Be both confident and humble at the same time. 

This is such a winning combination.

8. Don’t take rejection personally.

If someone isn’t interested in you, it might be because he/she isn’t ready to be involved, or they are involved with someone right now. I know it sounds strange, but dating isn’t personal! Your first date doesn’t know you well enough for it to be personal. Try to remember, it’s them, not you.


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9. Try to be patient.

I might be one of the most impatient people I know. And when I was dating after divorce at 40, I remember dry spells that felt so lonely, I could barely stand it. The dry spell will pass. Try to enjoy the peace in your life when you are alone, and try to learn more about yourself, and what you want and feel you deserve.

10. Remember that you are still healing from your divorce.

I always used to think that the reason I never met the right person until nine years after my divorce is because subconsciously I didn’t want it. I was still healing and fixing myself. I truly think that’s why I stayed single all those years. And that is perfectly OK with me!


Healing from divorce takes a really really long time. Let yourself go through the process. I’m not saying don’t date. I’m just saying to try to recognize that the pain of divorce, even if it lives quietly in your subconscious is there for a long time. Doesn’t mean you can’t enjoy life, just means that the pain needs to be dealt with in a healthy way.

11. Remember that 40 is fabulous.

I LOVED my 40s. I still looked young and felt amazing. Forties are the best because you get really smart. You are an amazing, wonderful person. Please believe that because it’s true, but also because what you think of yourself comes across in dating. If you think you are fabulous, then so will he/she.

 In closing, learning how to date after divorce at 40 isn’t easy, but it’s easier than you think. Try to enjoy it and learn from every date you go on. I wish you all the best!

Like this article? Check out, “Dating Someone Who is Hot and Cold Can Really Burn!”

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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

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