My Post-Divorce Dating Advice (Spoiler: It’s Not About Him)

Post-Divorce Dating Advice
Dena Landon

By Dena Landon | Jun 21st, 2023

Whether you’re recently divorced or it’s been a few years it sometimes feels like everyone has an opinion on your dating life. You’re dating too soon, and haven’t given yourself time to heal. Or you’re wallowing and have developed an unhealthy relationship with your Netflix queue. Instead of doing the walk of shame you’re seeing the screen of shame – Are you still watching? Press ‘yes’ to continue.

As much as I’d like to say that other’s opinions don’t matter, that you should just shrug it off, or roll your eyes, many of us emerged from our divorces or break-ups emotionally bruised. It’s hard not to listen to the constant barrage of commentary on your dating life and not wonder if you’re doing something wrong.

Even if your ex wasn’t verbally abusive like mine, I’ve yet to meet a woman who doesn’t have some insecurities – period. Which is why, as much as those well-meaning questions can sting, having friends that you can check in with when you’re dating again after divorce can be incredibly helpful.

For a long time, I didn’t trust my judgment when it came to men. I’d send screenshots of convos on OkCupid to my friends and ask their opinions. Does he seem cool? I feel like he might be hiding something. Until I learned to recognize the telltale clues of a cheater – vague answers to where he works when I ask for a good place to meet up for coffee, no easy to find social media accounts, sunglasses in his pics or all group shots (so he can claim it was a friend’s profile if his wife finds it) – I’d run the guys I was truly interested in by one or two of my closest friends. It still took me over a year of online dating hell before finding a guy I actually wanted to meet in person.

In that state of rebuilding our confidence, we do lean on the people around us for advice, support, and encouragement.

After we’d been texting for over a month, I’d seen his Instagram and vetted that he was truly single, and we’d established that, if all went well, I’d be going back to his place. Still, when I hopped on the subway, I brought a friend with me. That’s right, I, a thirty-plus year-old woman, brought a friend with me to the bar. (In my slight defense, the part of Harlem we were meeting in wasn’t the greatest). “If you don’t like him,” I told her, “I’m not going home with him.” To his credit, he didn’t blink when I texted him that I was bringing a plus one, politely bought her a drink, too, and impressed her so much that she waved good-bye to me at the subway and boarded the train by herself.

In that state of rebuilding our confidence, learning to trust our own judgment again, and forgiving ourselves for the mistakes we made with our exes, we do lean on the people around us for advice, support, and encouragement. There were three friends in my Facebook message string helping me choose an outfit for that night. At one point, when I freaked out and almost canceled the date, typing, “He photographs models for a living! Why the hell does he want to sleep with me?” a girlfriend I’ve known almost twenty years now typed back, “He doesn’t want to sleep with a model, he wants to sleep with you. Because you’re pretty awesome.” I still bought four different outfits for that night, but it helped.

If you’re lucky like me, the women in your life support one another and build each other up. In true friendships, you’ve probably served the same role for them more than once. The ring our exes slipped onto our fingers on our wedding days was meant to represent the unbroken circle of love, but since the day I took mine off the circle of women around me has proven ten times stronger than platinum.

In a month it will have been a year since that first post-divorce date. I don’t send every date night outfit through my friends anymore, though I do still ask their opinions on a guy when I start getting serious. I’m stronger, but I wouldn’t have gotten to this point without that initial support. Which is why, when I’m asked what advice I’d give to women re-entering the dating world after divorce, I don’t say anything about the bar scene, or which dating site is best. And I can’t really recommend bringing a friend along on your first post-divorce date.

Nope, I tell them, “Make sure you’ve got an awesome group of girlfriends around you before you start dating.” Make sure you’ve got a friend whose shoulder you can cry on when you get that first break-up text that makes you feel like you’re sixteen again (Telling me you weren’t sexually interested in me anymore? Low blow). Have a friend that you can send a screenshot of the response a man sent on OkCupid when you asked, “What are your other interests?” so that you can both laugh while you block him. (I was thinking museums, and movies, dude, not sexual positions!). And don’t forget to take them out for coffee to say ‘thank you,’ be there for them when they need you, and celebrate their presence in your life on Galentine’s Day and every day.

Dena Landon

Dena Landon

Dena Landon's bylines have appeared in The Washington Post, Good Housekeeping, Salon and more. The proud mom of a boy, she specializes in parenting and divorce.


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