I’d like you to meet your next husband

Reentering the dating game isn’t easy. Here’s how to rock your second lease on love

Mid-life dating feels like plunging blindfolded into the Arabian Sea. As a matchmaker, I’ve had many older clients tell me that they feel they’ve crossed over a time lapse, with zero understanding of this modern romantic jungle. Do you swipe, like, call or stalk? Is it weird that you prefer to have a phone conversation, when your match would rather spend hours texting? When is it okay to sleep with someone?

It’s like this: just yesterday, you were chuckling to a rerun of Seinfeld. Now you’re asking Google whether Sofia Vergara’s accent is real – because you don’t know if you love it, or hate it.

Everything seems confusing and the older we get, the more our personal experiences nudge us to stick to our guns with a take-it-or-leave-it declaration, even before we’re in an actual relationship. Like the spurned woman who believes that after her last relationship, the dating apocalypse is as real as climate change. Or the eternal optimist who wants a partner but only if she’s a vegetarian, 5’10”, loves dogs, and lives within four kilometres.

When I first met Shruti* early on a Saturday, I almost had to shield myself from her larger-than-life, happy personality. She was more enthusiastic than a twenty-year-old influencer who just got free hand creams. Despite a rough marriage, the 40-year-old marathoner’s sharp wit and physical energy (she’s training to scale the Everest base camp) left me significantly peppier. Positivity is infectious. It was no surprise to learn a few months later that Shruti found love. Who doesn’t want to be with a successful, adventurous and emotionally intelligent person?

If you’re looking for a partner, here are a few pointers to combing through the dating battleground without setting off any landmines.

Dating advice from a professional matchmaker

You need to be in a good place

‘You are what you attract’. Keep stereotypical judgements aside and be open-minded—because you don’t want to be a downer for yourself or someone else. If you’ve surrounded yourself with friends, annoying family, ex-husband or the neighbourhood watchman who feed your insecurities, the first thing to do is deep-clean your social circle. No kale smoothie can detox your disposition.

Take your time

The single people I meet in their 40s and 50s usually come with two kinds of life experiences – the first lot, who’ve been through marriage(s) and kids, are in no hurry to jump into another one. The other set usually hasn’t had much dating or marital history – they were busy ‘living’ or building their high-powered careers.

If I were to split the latter into two sub-groups, the first would include those who view dating like an Amazon Prime membership – the more, the better. Dating too many people at once can lead to real confusion – and ultimately result in nothing.

Also, if you have children (below 12) from your previous marriage, you should have an honest conversation with them first. Make a slow and steady introduction to this beautiful stranger in your life; because kids are smarter than they seem.

Know what you want

Now the people without dating experience usually ‘want a relationship’, but haven’t done anything to consciously change this reality in the last five years. Dates seem stressful and cumbersome. So ask yourself this: what kind of relationship do you want? Are you looking for a companion, casual sex or a partner who you can settle down with?

You know you’ve come of age when you can gracefully show the finger to pitiful neighbours and gossip huddles at weddings, despite your single status. What I’m really asking is, do you even want to be in a relationship? Make peace with your choices.

Choose a suitable medium

I remember meeting Rahil*, a single dad who had married his childhood sweetheart 25 years ago. While he had a wonderful relationship with his now ex-wife (who remarried and lived a few buildings down the road), his daily routine meant going to work (in an office full of men), coming home and then going for a run by 9:00 PM. He was clueless about how to engage himself or find a comfortable way to meet women. Sound familiar?

If you’re not an evangelist of the apps, ask trusted friends or colleagues to set you up. Attend a networking-style singles’ event if you know you’ll feel more secure in a room full of people, or opt for a service that works with your personal needs, and privacy. Choosing a route that makes you feel positive and comfortable, is half the battle won.

Be realistic

This one hurts many egos. I’ve met female clients in their 40s who yearn to have kids and inscribe this potentially complicated pre-condition in stone. I would think that one of the biggest allures of dating in your 40s and 50s, is not being able to hear the tick-tock of the biological clock. Take each day as it comes, focus on building your relationship first.

This brings me to the most important aspect: have the courage to stay honest, not just with your date, but yourself in the process. This will truly help you make better decisions about compatibility and what kind of relationship you’re actually seeking. Sure, you may blurt or hear awkward conversation starters, feel nervous on first dates, and freak out when you go away on your first trip together, wondering why you did all of it in the first place.

Most love stories unfurl slowly, not overnight, letting you quietly savour the smallest moments, and unabashedly celebrate momentous occasions. That is love.

And in the case of Shruti* (who’s been with her partner for over four years), it means you can climb mountains, together.

*Names changed to protect privacy

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