Gambitting: How To Approach Your Dating Life Like A Game Of Chess

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Sitting in her local Italian restaurant, putting the world to rights, Issy’s* Tinder date is going to plan. Her outfit of jeans and a nice top is fancy but "not too extravagant", her choice of carbonara is normal enough but "not too boring" and the vibe is "romantic but not intimidating", just like the Tripadvisor reviews had promised. You see, every aspect of her date has been planned — or at least as much as it can be.
"I have quite a Type A personality so I love planning, organising and having as much control over things as possible," says the 24-year-old from Wales. "I’ve never really questioned it in my dating life because it seems to be a natural extension of that."
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For Issy, dating comes with a strategy, every move determined by a desire to get things just right. And she’s not alone. Turns out, taking a calculated approach to dating is increasingly common — so much so that a new trend called 'gambitting' is on the rise, with recent research suggesting that 31% of single people, including one third of Gen Z, adopt the approach.

If you wanted to get your dream job, you'd plan how you'd get it. What's the difference?

Issy*
A gambitter may micromanage parts of their date — making conversation fun but not too personal, choosing a bar that’s lively but not deafening, securing post-date plans before the night is over — in order to construct the 'perfect' evening. Others may channel their attention into who they date, using relationships as stepping stones to find more refined partners in the future, a tactic also known as 'weekend updating'. Like a game of chess, interactions are calculated to the point of 'checkmating' the scene, or 'winning' at dating.
"It’s something I’ve always done. If everything is planned then I know that nine out of 10 times I’m going to have a nice time," says Issy. "It does take up a lot of mental space but if you want to get into a relationship, then what’s the point of being complacent about it? If you wanted to get your dream job, you’d plan how you’d get it. What’s the difference?"
Having a plan to navigate the early stages of a relationship is nothing new — reading one page of Jane Austen is enough to make that point pretty clear — but transformational psychotherapist and relationship expert Natalia Kobylkina tells me that the complexities of the current dating scene are causing some people to turn to gambitting.
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"With so many dating apps available people no longer want to waste time dating people who aren’t right for them," she says. "By micromanaging a date and planning your moves in advance you can anticipate your date’s next move and quickly ascertain whether the 'move' they make is right for you."
Dating coach Hayley Quinn has seen a change too, with the abrupt rejection associated with dating making it difficult to gain a sense of stability when entering a relationship. In 2016 Plenty Of Fish found that 78% of singles have been ghosted so it’s no surprise that people are wanting to reassert their power. "Modern dating can be tough: there's often a lack of clarity about what people's intentions are," Hayley explains. "As a result, it can feel like no one that you like, likes you." 
With its emphasis on getting ahead and maintaining control, Hayley tells Refinery29 that gambitting can be particularly appealing for people who have been hurt by previous relationships, when the desire to keep watch on everything is, naturally, high. "If you feel you constantly get messed around with dating, taking a strategic approach can seem like an appetising alternative to always feeling let down," she adds. "If you've been through the ringer, it can feel like a neat way to avoid ever having to make yourself vulnerable again."
After experiencing a string of "horrific" Zoom dates during the pandemic, 27-year-old Jodie from London unintentionally became a gambitter. From avoiding chain bars because they’re "boring, basic and predictable" to ensuring she locks eyes with her date for five seconds to see if sparks fly, Jodie's objective nowadays is all about designing an interaction to remember. 
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"I get a sense of fulfilment when I feel I’ve made a lasting impression. When my date says they’ve had an unforgettable time, it leaves me feeling empowered," she explains. Jodie says yes to dates with guys she knows she’ll never have a future with as she believes all dates are good practice, regardless of where they take her romantically.
Besides helping her avoid any disastrous dates, the model and DJ has found that laying out a blueprint for her dating life has had a positive impact on her mental wellbeing, removing the uncertainty from an undeniably vulnerable situation. "I have to have my life in order in every way because I suffer with anxiety. It’s always easiest for me to live via my calendar diary," Jodie says. "I’m also a perfectionist, so I don’t like to do things on a whim without planning them. I feel like it’s a missed opportunity."
Jen, 24, from Reading, agrees. Having encountered men who believed that she owed them something as a result of them making the first move, she turned to gambitting as a way of asserting authority — doing everything from being the one to suggest going for drinks to throwing in a controversial opinion or two to rein in the conversation whenever things got too intrusive.
"I’d always be the one to send a post-date text because I never wanted a date to think that they were above me. If I made the first move or planned the date, then they didn’t have a leg to stand on when it came to 'expecting' something of me," she says. 
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"It also gave me a massive confidence boost and was a major power move. If I arranged to do something I liked, then at least I'd have a nice enough time. It’s a super selfish way to think about it but I was dating for me, not for someone else."
After meeting her boyfriend using this more calculated approach, Jen heralds it a success. But gambitting isn’t for everyone, of course, and whether it remains a sign of an efficient dater or something more toxic, like most things, depends on what balance is struck. As Natalia explains, anything that makes us feel confident or clear in our objectives is a good thing. Having a strategy to help us find the right person is relatively harmless — healthy, even.
Problems arise, however, when these barriers become too high. When individuals get too caught up with the ins and outs of the 'game' to commit to the spontaneity that relationships demand, the essence of love itself is lost. "Dating is meant to be fun and if you’re too focused on sticking to your plan, you’re not only going to find the situation stressful but you’re not going to be the best version of yourself," says Natalia.
Three years into her relationship, Jen says that the calculated approach is a thing of the past. Now that she’s settled down, there’s no need to plan her every move. And while Issy is yet to find 'the one', whether she’ll give up the act when she meets her match is something she thinks about a lot, though she is "99% sure" that she will. As Natalia says: "Sometimes the best things are the things that happen unexpectedly."
*Name changed to protect anonymity

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