Sharon Gordon
Image: File picture
It’s a helluva week for death of famous and not so famous people. Maybe I’m just at the age when people from my generation start passing on. For those of you who only read my column, this week saw Dolly Parton, Tim Curry and Yayoi Kusama pass on. We also lost a casual acquaintance.
A good couple of years ago my bestie lost her partner and another close friend is dating someone who tragically lost their partner. We were comparing notes on what it’s like to either date someone in that situation or start again.
Restarting your romantic life after losing a partner is no small feat. Transitioning from a season of deep loss back into the world of flirting, first dates, and intimacy can feel equal parts daunting, bizarre, and believe it or not, if you let yourself, exciting.
If you are thinking about stepping back into the dating pool, here is a guide on navigating the fresh start with lightness, patience, and a sense of humour.
Dating may look very different from the last time you were single. The rules, technology, and expectations have evolved, but the core objective remains the same: connecting with another human being.
Embrace the Learning Curve: Modern dating often starts on a smartphone screen. Navigating swipe mechanics, digital small talk, and profile curation requires practice. View the process as an experiment rather than a high-stakes mission. I have heard some horror stories and there are scams a plenty. Extra vigilance is required. Don’t believe he’s stuck in Dubai with a stolen wallet and just needs a quick loan to tide him over or any version of that.
Curate Your Profile with Authenticity: Choose recent photos that reflect your genuine interests and personality (harder than you think if you hate your photo being taken). You don’t need to detail your entire life story in your bio; a warm, light-hearted summary of who you are and what you enjoy is more than enough to start a conversation. As a test I’d love to say, only reach out if you have money, interested in travelling at the drop of a hat, send a copy of your bank statement and passport to apply. I think I’d die alone. At the very least he should have his own home (or he’ll move in within 2 weeks), have a job (not a failing business), his own car (don’t believe the Uber nonsense), and has a functional relationship with his ex.
Set Low-Pressure First Dates: Keep initial meetups simple, a quick mid-morning coffee or a casual afternoon walk in a park. Short, low-key dates give you an easy exit if the chemistry isn't there and keep expectations manageable.
My take is, don’t have sex until you’ve had at least 3 dates. There are just so many people out there just for the ‘hook up’. If you’re one of them, no judgement here. But if you’re not, don’t get used. If you’re horny, we have plenty of ways to take the edge off without you becoming a notch on someone’s bedpost.
Having said that you may want to get the first time out of the way. Pick someone you have a vibe with, have sex just to be reassured that you’ve still got it.
Re-entering the dating scene doesn't mean you have forgotten your past; it simply means you are making room for your future.
Ditch the Guilt: Wanting companionship, fun, or physical affection is a healthy human instinct. Moving forward is an act of honouring your own life, not an act of disloyalty.
Expect Mixed Emotions: You might find yourself laughing on a date one moment and feeling a brief pang of nostalgia the next. That is completely normal. Hold space for both without letting guilt take the steering wheel.
Go at Your Own Pace: There is no universal timetable for when you "should" start dating again. Whether it has been one year or five, step forward only when it feels right for you—not when well-meaning friends push you to "get back out there."
The thought of being physically intimate with someone new for the first time in years can bring up a wave of nervous butterflies. Approach it with humour, open communication, and self-compassion.
I do want to say that the person dating you will have a hard time meeting the ‘perfect’ persona of your late partner. We tend to only remember the good about them. If you keep only remembering the good and comparing a fallible live human, you will never find anyone good enough. Every now and then remember the affair he had, the temper she had, the alcohol abuse. It happened, don’t wipe it away.
Communicate Openly: You don't need to give a full historical briefing but letting a new partner know that you are taking things slow or that it has been a while takes the pressure off both of you. Real connection thrives on vulnerability.
Keep Your Sense of Humour Intact: First times with new partners are rarely like movie scenes—they can be awkward, clumsy, or full of unexpected laughs. If a moment feels clunky, laugh it off. Humour is the ultimate pressure-release valve.
Focus on Being Present: Try not to compare new physical experiences with past ones. Every person and dynamic is unique. Focus on the sensory experience of the present moment rather than evaluating your "performance."
Dating after a major life loss is ultimately a celebration of resilience. Take it one coffee, one conversation, and one light-hearted step at a time.
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