After My Divorce, I Decided To Start Dating Again — And OMFG, Things Have CHANGED Since The ’90s

Here's what I've learned about dating in the era of eggplant emojis and Snapchat attention spans, when everyone is a Google or Facebook creep away.
dating after divorce: photo of a man and woman on phones Photo, Getty Images.

I can’t tell you about the exact moment when my heart broke. There’s no one definitive event that ended my marriage of 17 years. Like most relationships that have run their course, it was like a tire with a slow leak. A million tiny, undetectable injuries that culminate in the thing going flat and an inability to move forward. We were stuck, like so many couples in midlife, having spent all our energy on raising small kids, climbing career ladders and trying to fit square pegs into round holes.

So we called it. Deciding to separate was, in a way, one final act of love to save what was left of something once beautiful.

It’s been over a year since my kids’ dad moved out and I found myself sleeping alone for the first time in nearly two decades. At first, the sad feelings came often, numbed by binging Downton Abbey into the wee hours of the morning, chased with pots of coffee. Sometimes, when the kids were at their dad’s, I would be engulfed by a loneliness so deep that nothing could fill it.

No matter how good I eventually became at enjoying my own company, I couldn’t shake this longing to be in a relationship with someone who might think I was as awesome as I’d learned to see myself. For months, I’d looked into the face of any man I’d come across, playing a strange game of “Are You My Mother?” except replace “mother” with “soulmate.” After six months of celibacy, there were itches that needed scratching and an ego that needed boosting, so I decided to rip off the proverbial Band-Aid and throw myself into the world of dating.


Small snag: I hadn’t dated since the ’90s, not since Bill Clinton was impeached and the Goo Goo Dolls were a thing. The first iPhone was nearly a decade away. I had done some online dating back then, on a site called, when you were lucky if a photo of you existed on the internet. But how to date in the era of eggplant emojis and Snapchat attention spans, when everyone is a Google or Facebook creep away?

I hesitantly waded back in, creating a Tinder profile with encouragement from my BGF (Best Gay Friend) and regularly typing the phrase, “Am I ready to date yet?” into the modern magic 8 ball: the browser on my phone. (Pro-tip: If you need to Google this, you’re probably not ready, and that’s OK.) Now on my fourth dating app, I wouldn’t say I’m a pro-dater just yet, but I’ve had enough experiences (more good ones than bad) that I can now light-heartedly approach meeting new people, learning about what I need along the way. If you’re thinking about putting on your big girl pants and diving back into dating, here’s what you should consider.

Swipe right on yourself first

It’s important after a major breakup to take time to heal. I spent six months recalibrating, then dipped a toe into the dating scene and decided I wasn’t ready yet. I spent the next glorious six months dating myself, learning to do things like travel and go to concerts on my own before putting myself out there again. Yoga, therapy, time with friends and loved ones and journaling through the tough spots helped me fall in love with myself again and let me know, REALLY KNOW, that I could be on my own. Get to know yourself so you can be clear on what you hope to get out of dating. As a friend advised, “Learn the difference between what you truly deserve and what you are used to.”

Date outside your comfort zone

Ask yourself if your “type” has served you well. Chances are the kind of person you gravitated to at 22 might not suit the person you are now. Keep an open mind and choose from a diverse pool of dates, people with backgrounds and life experiences that may be different from your own. I look at each conversation and/or date as a unique data point, journaling afterwards to reflect on which traits and qualities are my must-haves, nice-to-haves and deal-breakers. Imagine you’re a journalist, and every date is an opportunity to collect stories. Ask lots of questions and try to be open-minded and non-judgmental about the answers, without ignoring your spidey sense when things seem amiss.

Don’t get discouraged by dating apps


I’m going to get real here. The behaviour on dating apps can be appalling. But perhaps more dispiriting than anatomically revealing photos you didn’t ask for is the use of emojis and acronyms in place of real conversation. You ask someone a question, and they answer. And it dies there! No reciprocal question. It’s like no one knows the rules of improv anymore and every conversation is a dead end. I wonder if prospective suitors are busy sprinkling breadcrumbs across multiple apps with many other women, or if they’re sending a quick text before going back to Candy Crush.

Dating apps aren’t the only way to meet people, but they do get points for reaching a wide pool of people in a short amount of time. Lots of my friends say apps worked for them, and that you find more serious potential sweethearts on the ones where you have to pay. I tried four different mobile apps before finding the one that spoke best to who I am (OK Cupid, fun for us chatty, writerly types). With two kids and a crazy co-parenting schedule, apps help me coordinate dates quickly around my availability and put the power in a woman’s hands (not everyone deserves a response).

Be efficient

Regardless of apps, blind dates or outings, trying to find someone you like enough to get to know better can be a huge time suck. Give yourself a window for which to cast the net, like: “I’m going to do this for two weeks and then delete the apps.” Or set times for soliciting or talking to potential dates, so that you’re not chatting distractedly throughout the day (breadcrumbs!).

You make a match. Great! But turning that match into an IRL date can be challenging. Be sure to ask if the person you’re chatting with is married (anecdotally, half of the men in the apps are married but only reveal it when asked), and be sure ask how he or she feels about kids (I have two and my baby-making store is closed). Putting your deal-breakers out there upfront saves you the agony of liking someone and having to end things because their lifestyle or vision for the future doesn’t match yours.

Express yourself


Whether you are looking for a one-night-stand or a serious life partner, be open about your wants as you meet people. Too often we try to conform, compromise or reveal only the best parts of ourselves just to make something work, worried we might “scare the other person off.” But remember, you don’t need to do that anymore. You’re a grown-ass person who is not going to change (not without a lot of therapy). Accept that there will be rejection on both sides while you try on different partners to see what fits you at this stage of your life. If you find that you keep taking it personally or can’t quiet the negative voice in your head, consider working through those feelings with a professional, such as a social worker or therapist.

Have fun! You’ve earned it

When I was ready to start dating again after my hiatus, I realized that I was putting too much pressure on myself to get the next partner right. The best part of mid-life dating is that you no longer have to make choices driven by your biological clock or that life list you constructed for yourself at 21. I don’t need someone to help me make babies or buy a house. Heck, I don’t even need to get married again. I can fill my limited free time with the wonderful circle of humans I have cultivated for myself.

Having a positive, up-for-anything outlook and a good sense of humour is crucial to weathering the ups and downs of meeting new people. Ask yourself if you NEED to have a serious relationship right now. “Not everyone has to be a life partner match,” my friend reminded me when I asked for dating tips. “It's OK to go out and have casual fun.” Having a series of short-term relationships doesn’t make you a failure, so settling down right away needn’t be your only goal.

Like anything new, dating after a long-term relationship is weird at first. But the more you do it, the easier it gets. The upside to having to kiss a lot of frogs is that you remember just how fun kissing is. Spoiler alert: SO FUN!


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