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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,