Love Again: 6 Real-Life Tips for Dating After Divorce

By: Karen Paul Holmes
Last Update: November 01, 2016

Infidelity, separation, divorce—they can tear you apart. You might doubt whether you can fall in love again. In hopes it’ll help you, I’ll share what I learned after my marriage fell apart. Though I’m not a relationship expert, experience can be the best teacher. I had been married for 32 years and was hurt to the marrow of my bones when my husband left me. How in the world would I ever have another relationship? I knew I wanted one, but the daunting task of finding the right person scared me to death. Here are five things that worked for me when I began dating after divorce:

1. Get out in the dating world again when you’re ready.

How do you know you’re ready? If you’re still feeling extremely hurt (crying in the grocery store) or angry (throwing your laptop across the room), or otherwise not through your grieving process, you’re not ready. But if you feel like you’re moving on, you’ve regained your independence, you are happy by yourself… then take the leap.

Even if you don’t date, at least get out socially – go to a concert, sporting event, art exhibit, whatever interests you. Enjoy yourself and increase your chances of meeting someone with like interests. Going alone will give you a sense of confidence, but if you’re the kind of person who can’t go solo, then recruit some friends to go with you. I bravely made myself attend a poetry reading alone when my husband and I were separated. I even took off my wedding ring, though I felt naked. Guess what? I ended up sitting with a couple of people who’d been in a class with me, and I also met new poet friends. It made me feel good about myself again – knowing I didn’t have to be part of a couple. In fact, I am still part of that poetry community.

At one point, I looked around an online dating site. My heart was actually beating hard with the possibilities, like a teenager wondering who’d take me to the prom. I saw a few profiles of interesting men. But then I freaked out, not able to imagine actually going on a date. That told me I wasn’t ready. A year or so later, after I had lived alone and knew I was fine by myself, I started dating someone I’d met through friends. I was ready; I wasn’t needy or on the rebound. I’ll admit: Dating after being married for 32 years was weird. It was fun, too, because I was ready.

2. Catch yourself when you're comparing.

You’re naturally going to compare your new man or woman to your ex. You’ll want to run away from anyone with the same characteristics that contributed to your marriage falling apart. You’ll feel drawn to aspects of the new person’s personality that are refreshingly different from the ex, even though in the long run, those things might be negatives. For example, if your ex was shy, you might be attracted to someone who is the life of the party. But being with that person all the time might be exhausting.

For me, being with a man who was totally accepting of me—metaphoric warts and all—was a new experience, and I learned that's what I wanted. I also wanted a happy man, in contrast to my restless ex who always saw the grass as greener on the other side.

Yes, you’ll be doing a lot of weighing of pros and cons. A spreadsheet won’t reveal the answer. You must use both your heart and your head. Try to look at the whole picture: How does this new person make you feel? How might he or she fit into your life? Will it be a total disruption (maybe one that’s needed) or will the new relationship slide right into the natural course of your life? On paper, my guy wasn’t Mr. Perfect, but he was the sweetest, most genuine man I’d ever met. Don’t expect perfection – it doesn’t exist. Take your time to really get to know this new person (see number 4). Even if you’re almost 60, like I was, you have a lifetime. And I’m going to guess dating someone later in life is a little easier than when you’re in your 30s or 40s. Sure, the older candidates have more baggage (as you do), but they have learned a lot too and tend not to play games with your affections.

3. Listen to your friends… but...

Yes, your friends will be a good set of eyes for seeing things from the outside, but they cannot know the intimacies of your relationship. Only you can decide who is right for you. However, if all your friends are concerned that you’re making a bad choice, pay attention. They might see warning signs that you can’t see. Some of my friends were concerned that I fell in love again too quickly. But for me, it worked.

4. Go slowly without fear.

A new relationship is exciting and scary. It’s scary partially because it requires an investment in time to get to know someone. (When do you invest time or cut bait before it’s too late?) It’s scary, too, because the initial excitement will not last. That doesn’t mean the relationship won’t be good, but the crazy, romantic, infatuated, falling-in-love part doesn’t last – reality sets in. The reality might be fine or it might be a rude awakening. Since you can’t predict the future, the only thing you can do is proceed with wise caution and courage. Fear will paralyze you. Do as the old saying says: “Take it one step at a time.”

5. Throw out old models and create something new.

You might just want to date and not narrow it down to one relationship. That’s okay too. One of them might turn into a permanent thing, or not  whatever. As my mother told me once, “If it’s meant to be, it will be.” Allowing a relationship to develop in its natural course is always better than forcing things too soon. I have a friend who had been divorced twice when she met her Mr. Right. They’ve now been together for years but don’t live together. There are no rules when it comes to creating the relationship that works for both of you.

6. Keep a journal.

If you’ve read my posts before, you know I encourage journaling or otherwise writing down your thoughts and feelings. It helps you get them out of your mixed-up head and into the light where they can begin to make sense or be tossed away as nonsense. Here’s a poem I wrote when I was just starting to think about dating again. It kind of proves you can have a sense of humor even when life seems as scary as getting on a plane when the flight right before it crashed. The poem is in my book, Untying the Knot.  

Mating Instincts

I’m not ready to jump
on the find-a-man bandwagon.
Haven’t had to since 25—
when (it’s said) my instincts chose
a mate whose genes mixed
with mine for the best offspring.
Yep, got a check-plus, gold star there.

What might I want at 56?
Rather than a handsome face,
long legs, high IQ, maybe
it’s  wisdom, longevity,
no adult son
still at home addicted
to Star Trek reruns.
But some men my age look like
how I remember Grandpa
(usually dozing in his chair):
wisps of yellow-white hair, scalp
spotted, Basset jowls, ear lobes
to his collar bones.
I can still smell the Old Spice…

Yet coupling instincts run strong.
With a mind of their own,
my eyes scan the left hand
of every man,
even those least likely—
my mother’s greasy-haired,
stressed-out gastroenterologist;
the 40-ish guy in red pants
pressing the elevator button;
the sewer repairman who,
at first heart-stopping glance,
looks like the one
whose midlife crisis caused mine.

-- Karen Paul Holmes

"Mating Instincts" first appeared in Falling Star Magazine and subsequently in Untying the Knot by Karen Paul Holmes

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