HomeNews‘I was sure they would fall in love!’ The dos and don’ts of amateur matchmaking
‘I was sure they would fall in love!’ The dos and don’ts of amateur matchmaking
May 13, 2022
Sarah, 45, describes herself as a “total Cupid” – “always single, and always connecting my single friends”. When we speak, she has just set up an old friend with a new one she met through yoga. “They hit it off straight away,” she says. She is waiting for a positive outcome from another pair too: “I haven’t given up on them yet.”
A generation ago, the Sarahs of this world were in heavy demand: your extended network was the first place you’d look for love. For a while, it seemed that technology had made them redundant: a 2019 Stanford University study showed the proportion of couples who had met through friends had plummeted, displaced by online dating. But, as the Tinder era enters its second decade, many single people are once again yearning for a more personal romantic approach. This could be why nearly 70% of respondents to a 2020 Pew Research Center survey said their dating lives were not going well.
“It’s become easy to meet, but harder to connect,” says Lakshmi Rengarajan, a New York-based workplace consultant at WeWork and elsewhere, who has been pairing people up for over a decade. Her goal has always been to “make dating more human”, she says. But the pandemic presented her with her biggest challenge yet. “All of a sudden, everybody had no choice but to use the apps.” In response, Rengarajan started the podcast Paired by the People, which is dedicated to reviving the art of the setup. In each episode, Rengarajan interviews a couple whose meeting was engineered by friends, or sets up strangers herself, with a view to showing listeners how they might go about it.
As confident as they might be about making connections elsewhere in life, says Rengarajan, many people feel unsure about how to facilitate or request a date, worrying it could be intrusive to offer or desperate to ask. “I think they have a very antiquated notion of what a setup looks like,” she says.
So, if you are single and want to be set up, how should you go about it? First, Rengarajan says, be clear about it with your friends – but only tell them the absolute deal-breakers for your potential partner such as sexuality or politics. “At the most basic level, it’s saying: ‘I am open to being introduced.’” Providing them with a laundry list of desired characteristics piles on too much pressure – and goes against the setup’s spirit of serendipity. “The language is important: don’t use words like ‘perfect’ or ‘match’ – even ‘good for me’ has a lot of judgment,” Rengarajan says.
The perfect phrasing, she suggests, is “someone you think I would get along with”. “Give them permission to go with their gut, and tell them that if it doesn’t work out, it’s not a big deal.”
By putting them at ease, says Rengarajan, you lower the stakes for yourself, too. Dating apps can make us so particular and quick to judge, she says, but if a friend has put in the effort of choosing someone for you, you are less likely to dismiss them out of hand. “People have a very low tolerance for awkward conversations. With a setup, I think your tolerance is slightly higher: ‘I’m not going to discard this person immediately – I’m going to at least let them finish their latte.’”
If you are finding someone a date, be thoughtful, but don’t overthink it. “Don’t ask yourself if they could get married, or even if they could spend eight hours together,” says Rengarajan. “Just imagine: would they get along?”
Rather than explicitly setting up her housemate and colleague, Imogen “deliberately and repeatedly” engineered for them to meet at social events. “I was sure they would fall in love: they’re both into philosophy and the same Korean restaurant in east London.” When they eventually went on a date, “I was so excited that my scheming and string-pulling had worked,” says Imogen, 32. But her housemate called it off abruptly, hurting her colleague’s feelings – “and now she doesn’t want to come round to my house any more”, says Imogen. “I sort of wish I’d left it well enough alone.”
But Imogen doesn’t think that a more considered setup would have had a happier ending – it might have made her feel even more guilty, she says. “I think that’s something you have to be ready for if you do an explicit set-up.
Rengarajan’s response to such disasters is sanguine. “What I always say to people is, your friends have sent you to bad restaurants, bad parties or bad vacation spots, and you didn’t punish them for that. I think good friendships can survive this.”
The introduction itself is crucial, Rengarajan says. Many people give recommendations, such as: “She’s a great friend,” which are too general to be telling. Sharing an entire relationship history, on the other hand, might extinguish a potential romance prematurely.
Instead, Rengarajan swears by offering a telling anecdote. “I can tell you ‘Bob is a great guy,’ or I can tell you ‘Bob is such a good friend, he helped me move into my fourth-floor walk-up apartment in New York in the summer.’”
Such stories prime the pair to see each other as rounded individuals, rather than just another date, she says. “It’s unbelievable how it changes the trajectory – they even start to look different to you.”
Bonnie, 36, encouraged her housemate to go on a date with her friend, and they are now married with two children. “I joke that the reason I suggested they invite each other for a drink was that they both have great taste in balsamic vinegar, and that Polly would be able to hold her own when Tom inevitably launched into a long conversation about international relations,” she says.
“In truth, they were simply both a couple of the smartest, most well-put-together and funniest people I knew – I just had a feeling.” And that feeling was reciprocated: “A nudge was all they needed – that first drink turned into a three-day date,” says Bonnie.
After making the introduction, you could check in to see whether your friends have made plans to meet (and give a gentle push if not: inbox overwhelm is real, says Rengarajan), or suggest a venue or activity. But the rest is down to them, for better or worse. “I don’t think you should feel entitled to an update,” she says.
It is natural to feel some trepidation about bringing friends together, Rengarajan says, but the worst-case scenario could be no more than slight awkwardness. “You will survive running into an ex, or having to rearrange your dinner party.”
In fact, involving more people in your search for love can make it feel fun. On one episode of Paired by the People, Rengarajan interviewed a woman who roped her friends into finding her 12 dates for her “date of the month club”. “I’m not looking for Mr Perfect, I’m looking for Mr November,” Jenny Tolan told them in her explanatory email. Her friends responded with enthusiasm – and Tolan ended up marrying Mr July.
For anyone burnt out by dating, Rengarajan says, this approach can be refreshing. “People think it’s this big production, and it’s not. You can have fun with it.
“We do know how to do this,” she adds. Our instincts might be rusty – “but I don’t think they’re gone”.
Sarah, for one, is confident that her latest introduction will eventually pay off. “I think it’s a match made in heaven … I wish a friend would do it for me.”
Case studies’ names and some identifying details have been changed