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Getting Back In the Game When You've Been Benched for Years

Updated: Oct 3, 2021

Some cheerleading and a few of our favourite tips for when you think you’re ready to try love, sex and intimacy again.

"I know nothing about sex, because I was always married." Zsa Zsa Gabor

Let’s just get right into this, shall we? It is downright terrifying to think about being naked with someone else after years of marriage to the same person.

There is no shortage of things that can add extra layers of terror:

  • you and your ex jumped off the sex and intimacy train years before officially calling it quits

  • you carried and birthed babies and have all the marks, scars and pouches to prove it

  • you are over 40 and now gravity and hormones are playing sick and twisted competitive games with your body on a daily basis.

Extra points if:

  • you met and married your partner before Brazilians were a mainstream thing

  • the last time you bought "sexy lingerie" it was from a grocery store

  • you last dated when the Internet was so new you could only meet a partner organically and in the wild.

In short, many of us are not versed in the etiquette of modern dating. Everything is new and scary, and we are painfully aware that we don’t even know what we don’t know.

We might be ready for love, sex and intimacy, but we’re also now back in the dating pool with women 20 years younger than us who invented modern dating.

It’s intimidating to say the least.

Would it make you feel better to know we’ve been there? And that we survived?

And even better, we know lots of other women who have entered the modern dating world after long, long periods of time on the bench, who are enjoying playing the field once again.

So if you’re ready to step out of your practical, full-coverage cotton undies and into a new pair of silky big-girl dating pants, we share some of our favourite tips that got us back in the game.

Find yourself a modern dating mentor

Make a beeline to any recently divorced friends you have, as they’ve probably already tried this a few times, plus they'll be able to entertain you with ridiculous stories of what has gone wrong and, hopefully, what has gone right. Even if you decide online dating isn’t for you, your friends who have put themselves out there and gone on a few dates, can tell you what to expect and how to prepare -- and maybe set up a blind date or two!

It's always a good idea to get several perspectives -- find a younger colleague at work or a friend at yoga, preferably a millennial, who can walk you through online dating and creating a decent profile with compassion but also practical knowledge. Ask them where you set up these dates for your safety and how to create an exit strategy if things don’t click or just feel weird. Like, maybe save the hike in the forest without cell service for the 3rd or 4th date.

Ask your mentor all your questions; get it all off your chest: Should I disclose that I have kids on my dating profile? Should I say “casual” or “something more” when they ask me what I’m looking for? How long do I have to wait between messages to spark interest without seeming needy? What questions can I ask that sound flirty and fun but are really a way to test them for red flags? If they can’t spell or take the time to use punctuation, can that be enough to call it quits?

Do a dry run on your dating outfits

Okay, you've done it. You've swiped right, agreed to a blind date, or bumped into an old high school flame who is also miraculously single and the date is on the calendar - cue wardrobe panic!

Try everything on with your friends or text them pictures. Focus test those tight jeans, that plunge-neck blouse, those heels you bought 17 years ago but never wear. You’ll be surprised how much you have forgotten about getting dressed up to hopefully get undressed. Your friends know how to boost your confidence, what bra looks best with that blouse, and what size you wear so they can lend you some of their clothes in a pinch.

And if you are lucky enough to have a true bestie, she’ll speak the honest truth about the state of your bras and underwear, and take you to Winners, or point you online to Simons, to buy 7 pairs of new, sexy ones for under $25. It’s a scene right out of Bad Moms, but it happened to us, and thank god it did. It’s amazing what you get used to wearing when no one is looking.

Have some real self talk about your insecurities

Just contemplating going on that first date again means having to think about how you look close up and naked, and nobody we know wants to do this. After years of already having had your younger body reviewed and accepted by a long-term partner, it can be an incredible act of vulnerability and courage to put your older, more travelled body out there for assessment once again.

If sex and intimacy is indeed your goal, but also your greatest fear, you are going to need to face this one head on.

If you have kids living with you, ask other single parents how they manage to carve out a little privacy for dating and sex with custody schedules, possessive exes, or worse, nosy kids who notice EVERY new number and message that pops up on your phone.

Complain to your friends that the extra layers of skin over your body make you feel like you're zipped inside a postpartum jumpsuit you can’t seem to take off. The good ones will commiserate and help you accept your beautiful self right where you are at this point in life, and remind you that many of the people you’ll be dating are at the same point, with the same insecurities. The extremely good ones will tell you from experience that love, sex and intimacy the second time around and later in life might just be the best kept secret in town.

After all, half the battle to dating again is conquering your nerves—and tales from the real-life trenches can put things into a much more manageable perspective.

But really, the most important thing you need to get through the first few encounters is a sense of humour. If you are able to laugh at the pre-game antics, what happens during the half-time show and in the locker room after it's all over -- then you're ready for whatever play the other team throws at you.

Do you have questions about dating or funny stories you'd like to share (anonymously, of course)? Email us at and we'll use them in upcoming posts!

More resources for getting back in the game

Upcoming unhitch events

We offer affordable access to the experts on family law, financial health, real estate, health and wellbeing and more through our Live Q&A Events. Browse and register for our upcoming events—these one-hour virtual gatherings are an ideal way to get a friendly overview of separation and divorce from professionals in the field. Members get a discount on all events and the opportunity to submit questions ahead of time to our speakers.

Other resources

Read: Modern Love, the beloved New York Times column featuring real stories from real people who are right where we are, and a whole lot more.

This long-running column is so brilliant and popular, you can also now listen to it via podcast, read it in a book, or watch the mini-TV series. We recommend all of them, obviously. You’ll thank us.

Watch: 6 Reasons You Choose the Wrong Partner by modern philosopher and author Alain de Botton.

We love his sharp insight and dry humour, and his thoughts on love, marriage and why we are so bad and picking the right romantic partner make for a deep and comforting dish of self-reflection.

Key episodes, which are also listener favourites, for anyone needing the down low on entering the dating scene include “How to Harness the Power of Peak Dating Season” and “Dating after Divorce”. In both, Kate Anthony is joined by Bela Gandhi of the Smart Dating Academy for a lot of humour, real-talk and insight on everything from how to navigate online dating successfully to what red flags to watch for on your first few dates to the realities of dating in a COVID and post-COVID world.

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