Dating After Divorce: Advice, Tips, and Why This Is An Exciting Time!

dating after divorce

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

            Dating after divorce is something many people dread (I definitely dreaded it 11 years ago.) In fact, a lot of couples decide to stay together (not get divorced) because neither wants to start dating again. I mean, isn’t that why you got married in the first place? Because you enjoyed monogamy and didn’t want to go on awkward, uncomfortable dates anymore? So, why would dating after divorce be appealing?

Who wants to put themselves out there again, be vulnerable, take chances, spend time with people you know in the first two minutes aren’t for you, or face rejection, i.e. go out with someone you really like only to have the person never call you again? Thoughts of dating after divorce can feel hopeless, depressing and just plain scary.


But here’s the reason dating after divorce can be appealing: The chance to find true love. If someone was married, that person obviously enjoys marriage/monogamy/a partnership. He or she was just married to the wrong person or was in a situation that wasn’t working. So, wouldn’t it make sense that the person would want to try marriage again, this time with the right person? For that reason, even with all the negative feelings attached, and all the frogs a person has to kiss and all the heartbreaks that go with new relationships, dating after divorce offers the hope of finding love again—maybe the deepest, best love you’ve ever known. I mean, how are you going to meet someone significant if you aren’t willing to date? You aren’t. The bottom line is, you have to endure a little pain (and a lot of patience) to get the big payoff.

 I get so many emails from divorced men and women asking for divorce advice for dating again.

“Where do I begin in dating after divorce?”

“How do I start dating again?”

“How do I do this?” 


Here is my answer: START WITH YOU. Start by liking yourself as you are, and accepting yourself as you are. Let me explain.

I was 16 when I started dating. I met my now ex-husband at 33 and was married at 35. I then started dating again at 42. Dating at 42 is a heck of a lot different than dating at 16 and up (before marriage). At 16, and in my twenties and even thirties I felt untainted, happy-go-lucky, prettier, skinnier, and had no bitterness or baggage or history of anything bad at all really. At 42, let’s start with looks. I had: wrinkles, sagging skin, a muffin top, varicose veins, not to mention a broken heart and baggage. That said, 42 had its pluses. I found myself with more wisdom, compassion, I was more interesting, I was funnier, and I still felt physically attractive, but in a more mature, confident way.


Maria Spears - Dating and love coach


I met someone at 43, and dated him for 6 years before we broke up. So, I then started dating again at 49! This time was even worse. I had more wrinkles, a bigger muffin top, more varicose veins, and more baggage. I also began having some health challenges (typical age-related). But, at 49 I also had even more wisdom, compassion, I was even more interesting, AND I found gratitude and peace. I was gentler, less impulsive. I felt smarter, I really liked myself, and I was proud of myself from a professional standpoint and as a mom.


The key to dating after divorce and/or dating at an older age is to love yourself for all of your wonderful qualities and accept things as they are. That’s not to say you should eat burgers and fries every night and accept that you are larger. But rather to accept that perfection isn’t realistic nor is it necessary. Effort, gratitude and self-love are so much more important than perfection. Be who you are, but be the best of who you are–the person you really really like and respect. Then, what others think won’t matter so much.


Now let’s get down to specifics.

Here are my 15 dating after divorce tips:


1. Online dating apps and dating sites are great! That is how people connect these days. Accept it and embrace it. Don’t take it personally if someone doesn’t respond to you. Remember, it’s a couple of small photos. How can they really get the real picture of you? They can’t.  Swiping right and left is so quick that some people are going to pass up great people—like you. Also, please be careful. Never go home with someone you meet online until you know him/her really well and always take your own car or Uber to the dates.

2. First date advice: go in with the attitude that you are interviewing your date-not “I hope he/she likes me.” Keep conversation relatively light and do not badmouth your ex or talk about your divorce. Think of the answer to the question: “Why did you get divorced?” Know what you are going to say. Sugarcoat it but don’t lie. Plus, no one wants to hear “My asshole ex owes me $1500 and refuses to pay. I hate that dickhead.” Or “My effing ex wife is a slut who cheated on me and doesn’t care about her own effing kids.”

3. Think about selling your ring. I recently received an email from a guy who said he went out on a date with a divorced woman who was wearing her engagement ring (on her left ring finger!) To me, that says “I can’t let go of the past.” Selling your ring can be liberating and empowering, and help you move on. I know it is a beautiful piece of jewelry, but at this point, it’s just a material item that might hold you back if you keep staring at it (or wearing it.)


Grace Untethered - Holly Herzog



4. It’s OK to talk about your kids, but also talk about yourself. In other words, don’t let your kids define who you are. The guy (or girl) is there to find out about YOU.

5. Your phone needs to go in your purse for the entire date without checking it. Guys, phone in pocket. The biggest turnoff is when you are telling a story and your date is looking at his or her phone.

6. Be open-minded. If at first sight, you don’t want to rip his clothes off (or have any desire to kiss him) it’s OK. Talk to him (or her.) You might surprise yourself.  Attraction comes from the inside.

7. If he doesn’t call after the date, don’t take it personally. It could have NOTHING to do with you. It could be bad timing or something with him. It just wasn’t meant to be. Disappointment is part of dating. Always has been.

8. Don’t have sex on a first date. Please. It’s just cheesy. If you find the lust is out of control, kissing is so much sexier (and classier.)

9. Try not to judge. Remember that this dating after divorce thing isn’t easy for people. Someone might be really nervous and say something stupid. No one is perfect. Give him a break.

10. Be honest. If you don’t want to go out with him again and he keeps calling, just tell him. Don’t lie and say you got back together with an ex boyfriend. Just say, “I don’t want you to waste your time and this doesn’t feel like the right fit.”

11. Have fun! Don’t put pressure on yourself to meet husband (or wife) #2. Take one date and one person at a time. You deserve to be really picky and not settle this time around.

12. Recognize red flags. Drugs, alcohol abuse, a mean streak, lying. If you see it once, it’s going to happen again. Rationalizing someone’s behavior isn’t a good option.

13. Don’t be afraid to be vulnerable after a few dates. It’s very scary but if you want a REAL relationship, you need to open up and show the real you. When you see that he/she likes the real you, your relationship will get even better. And if he doesn’t like it, (which he will) but if he doesn’t, then he isn’t the right guy.

14. Be understanding about the person’s kids. Kids have to come first—both his and yours. So, if your date gets cancelled last minute because of a kid issue, deal with it. That’s part of dating after divorce. If his/her kids don’t accept you, it isn’t personal. Don’t resent them. It’s not their fault.

15. LOVE him (or her.) This time around, show your new person that you adore, appreciate, admire, respect and value your time with him or her. Don’t take him or her for granted. That said, on the flip side, don’t put up with him or her if he’s not treating you the way you feel you deserve to be treated. It’s also way too late in the game for that!


Dating after divorce really is scary, but don’t tell me there’s not a part of you that feels a little bit excited at the promise of meeting someone and falling in love again. It’s OK to admit it! If you are newly separated or divorced, you’ve probably felt lonely for a very long time, so dating after divorce offers the potential to find friendship, companionship, laughter, warmth, deep love, and a meaningful bond. I wish that for everyone who wants it. What’s so beautiful about humans is that our hearts, even after being broken have the capacity to love again, and love in an even deeper and more meaningful way. You might surprise yourself. You might not have met the love of your life yet!

Like this article? Check out, “3 Words For Those Who Fear Dating After Divorce”


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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.

    6 Responses to “Dating After Divorce: Advice, Tips, and Why This Is An Exciting Time!”

    1. Marianne Plude

      this is very helpful information, my issue is I don’t like on-line dating so where would one start to meet potential dates?

      • Stephanie Spencer

        Are you a part of a church or other religious organization where you could meet someone? Maybe ask your friends if they know anyone? Or sometimes just going out by yourself…sit in coffee shop, cafe, go to outdoor activities in your community. Dress cute and look approachable, smile and make eye contact. You never know who might strike up a conversation with you or vice versa. I’m in the same boat as you. Recently seperated 3 months ago and not even interested in dating again… for now. But once I am, my above suggestions are what I plan to do.

    2. Terri Taylor-Staley

      Great article! I’ve been divorced 11 years now because I rushed into marriage the first time. I had the baby fever bad and the bio clock was ticking! I have been raising kids and dating on and off during the last 11 years. I am still hoping to find the love of my life and this article is encouraging. Some dates were from my church single adults class, and some from online dating. I have tired of online dating now because the majority if the men there are just looking for free sex. I am planning to go out and work as a volunteer for community events. It seems like a good way to meet good people. 🙂

    3. Anne Marie

      Thanks for being such a great online resource for dating after divorce. I’m going on my first date this Friday night after being separated and then divorced more than a year ago. I’ll follow the dating advice steps that you suggested for divorcees. Wish me luck!

      • Jackie Pilossoph

        Awww, good luck! But, you don’t really need it. Just be yourself and if it doesn’t go well, what have you lost? Nothing!! Try to enjoy it and have confidence in yourself–both inside and out. If he isn’t interested, it’s not personal. If you aren’t interested, maybe he could become a platonic friend. Or, maybe sparks will fly!! I hope so!


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