How to Date After Divorce

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Hey Wendy,

I’m getting divorced after 20+ years of marriage. Our kids are grown. I just found out he was cheating on me, and now he’s moving in with her. They’ve been together nine months.

While shocked, I’m completely over it and moving on. I don’t feel like there’s anything to say, and I feel free. So, my question is how long should I wait before I start dating? I’m in my forties and I’ve never been taken out on a date before. My husband and I just sort of hooked up and then we were together, so I don’t really know what I’m doing. Thanks for your advice.

Deb G.


Hey Deb,

Hold up. I hear you when you say you’re completely over it, moving on, and free. I can relate to the lightness you feel from a weight lifted, and it is indeed freeing. But you’re dishonoring yourself when you say you’re “completely over it.” What you just went through is hard. Twenty-plus years of marriage is nothing to sneeze at. That’s a whole lot of your life, your time, and your heart invested. Your reality has been shaken to its core. Let’s take a breath to acknowledge that, shall we?

I have a three-part plan for you to move on powerfully:

Note: If you regularly read my column, you’ll know my answers aren’t designed to sell you stuff, but you happen to fit neatly into the sweet spot where I have a ton of help ready-made for you. So, I’ll recommend a few tools along the way, and I’ll also give you a bunch of free advice and tips. Here we go!

Part One: Start to clear out the past hurt. I know you think you’ve released this and you’re ready to move on, but humor me here. Your hurt feelings, the relationship’s injustices, and his all-around assholery need to be voiced and processed with someone you trust who’s ready to listen. This will help you release any pain you might be unconsciously holding onto or might be trying to bury. Don’t skip this process on the way to a new life.

Here’s how. Grab a trusted girlfriend who’s a good listener. If you don’t have one, you can hire me for an hour as a plan B, but I cost way more than your girlfriend does. Grab your friend and ask her to do some reflective listening. The two of you sit together (in person, over the telephone, over Zoom, whatever works for you), and she listens while you unload in bite sizes. Tell her, in the words most authentic to you, what he did and what happened, just a couple sentences at a time, so she can reflect it back, starting with, “I’m so sorry _____ happened.”

If your friend is good at this, she’ll tap into an empathetic space to really feel what that was like for you, so when she speaks the words back to you, the “sorry” feels real (because it is). When our wounds are witnessed and really taken in by someone, we have a greater chance of truly letting the harm go. Do this with said friend until you feel the grip of your past relationship loosen, and you start to feel more spaciousness in your heart. If it’s not working or you don’t feel you have enough information to do it right, move on to Part Two.

Part Two: Learn to date. The fun part! Grab my Ready for Love workshop (it’s pre-recorded and ready to go, so you can just download the audios) because I’ll not only walk you through how to date, I’ll teach you how to not waste your precious time and energy along the way.

This course also gives you in-depth instructions on how to do Part One, btw.

If that feels like too much information, here are a few dating tips:

1) Date online — it’s nearly impossible to meet someone in the “real world” these days, and you’ll have better odds with someone you have stats on up front.

2) Don’t wait for guys to reach out. Go find who you want to date and drop them a line and see if they come after you in return.

3) Don’t settle for the cute one who’s paying attention to you just because he’s cute — make sure you have real compatibility. Which leads me to…

Part Three: Sort out who’s right for you. Yep, there’s a course for this, too. Partner Have-to-Haves will help you figure out who’s a good fit for you, and what you might look for in a compatible partner — I mean besides six-foot-four and bedroom eyes (obviously). Not ready for this yet? No prob. Here are two places to start for sorting:

What are your deal-breakers? You can tell you’ve got a deal-breaker if you would rather live alone than live with (or without) that thing. Smoking is a common one. Make a list of ten deal-breakers before you ever go on a date. This way you can see red flags that need to be addressed when the cute and charming one comes along and blinds you to everything else in the moment.

What are you dying to provide in a partnership or to a partner that is empowering? If you’re dating someone and the gift you most want to give is something he doesn’t want to receive, you’ll be sadly disappointed and feel underutilized as a partner.

You are starting from scratch, which can feel daunting, but I’d like you to consider this as a clean slate. An opportunity to build a strong, intentional foundation for a relationship from the very start. Amazing, cooperative, well-matched partnerships don’t happen by luck. And partnerships created by design instead of a “Hey, you’re cute, let’s do this” scenario have a way better shot at a healthy, happy lifespan.

Good luck out there!

Wendy Newman is the author of 121 First Dates. She’s a dating, sex, and relationship expert who’s led hundreds of workshops and revolutionized the lives of over 70,000+ women internationally.

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