Dating After Divorce: How to Do It the Right Way
Dating after divorce can feel like stepping into a strange new world—especially if you’ve been out of the dating game for a long time. You might feel like the dating pool has changed, the rules are unclear, and your comfort zone is nowhere to be found. But here's good news: not only is it possible to find a healthy new relationship, it might be the best thing that’s ever happened to your love life.
Whether you’re a newly single mom, a long-time single person, or just someone who’s survived a difficult long-term relationship and is finally ready again, I want to offer a path forward that is honest, empowering, and (yes!) a little bit fun.
Let’s tackle post-divorce dating the right way—without dragging emotional baggage along for the ride.
First Step: Tell the Truth About Your Past Relationship
You're not imagining it, everyone has baggage, and that includes you. You can't help but carry around your past. The most effective, happy daters do the work to come to terms with their past relationships.
The first step: Own your story. That means telling the truth—not just about your previous marriage in general--when and how it came to an end, but about your part in it. Did you stay silent when you needed to speak up? Did you pretend you were okay when you weren’t? Did you stay for the kids or the lifestyle? Did you make some of the same past mistakes you now want to avoid?
Too often, we lie to ourselves before we ever lie to others. That’s where the healing process starts—by identifying how we withheld, avoided, or chickened out in our own lives. It's not about blaming yourself; it's about bringing a level of understanding and forgiveness that ACTUALLY helps you discontinue the pattern.
As a dating coach, I don't just make sure my clients know how to date effectively; I make sure they don't repeat their past mistakes.
Next Step: Play Past Relationship Connect-The-Dots
It's very likely that whatever happened that caused your divorce has its real roots in your family of origin. It's also possible that you've been repeating the same type of mistakes when looking for love over and over, not just in your marriage. And you are likely to repeat them again if you are not crystal clear about them and how to avoid them.
Getting clear about your patterns requires something far beyond talking to a therapist. In my work, it all needs to get written out and charted and then discussed with the people closest to you. The first step is to be accountable to yourself about your negative patterns, and the next step is to be accountable to the people who love you. When you explain it to your friends, your kids, and even your parents, you find out some things that you didn't know.
1) They probably already knew your patterns
2) They probably have similar ones (which is part of why it keeps happening)
3) They want better for you
4) Forgiving mistakes (including your own) is possible if you fully see them, own them, and make an (accountable) plan to fix them
5) Talking about it from a place of ownership makes you feel better
Phew. Bad news: this requires humbling yourself, and that can be hard. Good news: there is a path to choosing better next time, and it works!
Let Go of the Past to Create a New Life
Part of reframing past mistakes is deciding that they are going to be what makes new, healthier love possible, not what's going to stop you from finding new love! You can't let go of the past until you understand it, reframe it and learn from it.
It's normal to have emotional baggage, fears, and limiting beliefs that keep you stuck. Whether you were married to a narcissist, dealt with a major life change like a health crisis, or just feel like it’s been a long time since you’ve had a deep connection with a partner—with the right self-reflection and acceptance, you can let that all go.
In post-divorce dating, you will need to tell your dates about your past, but in a way that suggests learning and growth. You need to have let go of your past enough that you can talk about it with ease and wistfulness, not with bitterness and angst.
The Best Way to Talk About Your Own Divorce
How do you explain the end of your marriage to a new person without sounding bitter or broken? Tell the truth—with balance. Don’t play the victim or demonize your ex. Talk about what you learned, what you’ll do differently, and what kind of future relationships you're looking forward to now.
This matters whether you’re on a second date or just texting with a potential match. The idea of dating becomes less scary when you have a clear, truthful story about your past relationship that reflects your growth, not your regret.
Good news: Did you know that people find divorced people more trustworthy to date than people who have never been married? Dating in midlife as a divorcee has the advantage of you being perceived as someone with life experience. You’ve had a chance to figure out what doesn’t work for you. Now, you’re ready to focus on what does work.
A Better New Partner Starts With Self-Trust and Intention
Sometimes your past mistakes can cause you to lose trust in yourself.
Before you put yourself out there on dating apps or head to social events to meet new people, ask yourself: Do I trust myself to choose a good match? If the answer is no, that’s understandable. It's a good thing the past doesn't predict the future; however, it does mean you have not yet done the work to "fix your picker.”
Your ability to spot red flags, use your gut instincts, and stay grounded in your own needs is your best way to avoid falling into the same old traps. Make a list of what you want and stick to it.
You can’t spot a wonderful man if you haven't even conceived of what one looks like. You can't find true love while pandering to your fears. The only way to build a romantic relationship that lasts is by building one on trust and truth—first with yourself, then with potential partners.
Online Dating and the Modern Dating Scene
Online dating has opened up so many different ways to meet new people. You can connect through dating apps, join a Facebook support group for divorced people, or try meeting someone at coffee shops, through old friends, at events, or while engaging in new hobbies.
Try not to get overwhelmed by the enormity of it all. You need a strategy for how to approach all the choices when you are newly single and how to navigate all the lying that is going on on the dating sites. More about safety here.
But please remember the dating scene is full of single men and women who are just as scared and hopeful as you. Most people on the sites are earnest and looking for a real connection. Your job? Show up as your whole self. You don't need to lead with your divorce papers or personal information, but you do need to be real. Honesty is sexy. And it’s the foundation of every committed relationship worth having.
Casual Fun vs. Finding Love: What Are You Really After?
There’s nothing wrong with casual fun, especially if you have been in a loveless or sexless marriage for a long time! If that’s what you want, be clear about it in your profile and when you meet people. There are plenty of other daters in the same boat! But if you’re looking for a long-term committed relationship, possibly a future husband, you must be clear on that intention.
People fall into different camps, and you should never set yourself up to be the person who tries to change someone's camp.
Some people are ready for a committed relationship. Some people are open to second marriages. Some are not! Please do not enter the dating world until YOU are clear which camp you are in right now. You can change camps, of course, but the best way to date is different depending on your camp.
Any new partner deserves to know which camp you are in, however I suggest you ask them first (In terms of dating in general what are you looking for right now, casual or long term?) because that way you are more likely to get the honest answer vs. the one they think you want to hear.
If you are following my 3-date strategy you'll know you only have until Date #3 to get this topic sorted out!
New Experiences Require New Friends and New Boundaries
If you're serious about doing dating differently this time around, you may need to reevaluate who you let into your inner circle. That includes toxic friends, single friends who discourage you, or even old friends who can’t relate to your new goals.
Instead, surround yourself with people who support your growth. That could be a coach, an online dating group, or even a local meetup of divorced people in your city. Just make sure you’re not taking advice from folks who haven’t healed from their own divorce process.
Reclaiming Your Voice on the First Date (and Beyond)
If you spent a lot of time in your marriage keeping quiet—about your desires, your dreams, your needs—this is your time to reclaim your voice. Start as you mean to go on in early dating. Prove you can do it differently this time.
On a first date, don’t be afraid to ask deep questions. If you notice something off on a second date, speak up. If someone pressures you to move too fast or share too much, trust yourself.
There’s no real “right way” to date after divorce. But there are better ways. Honesty, curiosity, and the courage to be your full self are what get you there. You got this!
Frequently Asked Questions About Dating After Divorce
1. What’s the best way to start dating again after divorce?
The best way is to start with yourself. Reflect on your past relationship, take time for the healing process, and get clear on what you want. Start small—maybe online dating or coffee with a single friend’s referral—and keep your expectations grounded.
2. How soon should I talk about my divorce with a potential partner?
There’s no perfect timeline, but the first few dates are a good place to share a high-level version of your story. Keep it honest but not too detailed, and focus on what you’ve learned, not what went wrong.
3. How do I avoid repeating past mistakes in new relationships?
By taking an honest inventory of what didn’t work in your previous marriage. Know your patterns, your red flags, and your deal breakers. Get support if you need it, and don’t be afraid to pause before committing again.
4. Is online dating a good idea for divorced people over 50?
Absolutely. Dating apps can connect you to lots of people you’d never meet otherwise. Just be discerning—look for emotional availability, honesty, and someone who’s truly ready for the next step.
5. What if I’m scared I’ll never find real love again?
That fear is normal—but not a fact. Plenty of divorced people go on to find true love, even after a long time alone. Keep an open heart, surround yourself with encouragement, and take things one step at a time.
Love,