Dinner Club#2: So much for serendipity

Hello Dinner Club fam,

A question that I keep getting asked all the time is “How will you scale this?”. Honestly, I’m not sure I even want to. There are several bits of what I do that will simply be ruined at scale. Honestly, how often do you go out to a friend’s party, and meet someone awesome? Once a month? Once a week? Every day? 50 times a day? If I scaled this, it wouldn’t be serendipity, it would be Tinder.

This is a very hit or miss type of niche experiment. It will appeal to those who are open to the possibility of meeting interesting people without judgement, preconceived notions or check-lists. This is not yet another dating app that you sign up to because you want to “maximise your odds”. I know that each of you is on a different journey - some to date, some to marry and so on, but it doesn’t matter.

What matters is how you meet. If you want serendipity to bring you together, you’ve got to give it a chance.

About Thursday night …

This week was special. Not just because I organised more than double the number of dates as last week, but one of them was a celebrity date! If you thought meeting new people to date was hard, talk to someone in the public eye - it’s 100 times worse. So, I am just glad that I was able to connect two wonderful people who would’ve found it hard to meet otherwise.

Here’s what some had to say after the date:

  • is it possible for dinner club to keep in mind what kind of person am looking for before am making a match?

  • It's perfect as is. Curated and niche :)

  • Trial and error. I am sport enough to be a guinea pig.


This has been a heavy week. I’ve learnt tonnes this week:

  • I wish I were an algorithm, at least I wouldn’t be such a big mush ball and have my heart broken so many times.

  • The randomness and sporadic nature of your dates isn’t a bug, it’s a feature. The blind bit of the date isn’t a bug, it’s a feature. Not having to filter or swipe is a feature, and not a bug.

  • If you’re on Dinner Club, but you’re a sucker for efficiency, your needs may be better served on Marriage Broker Auntie. I received this yesterday from someone who worked with me over the last three months:

    “After having spent a significant amount of time and money skimming through countless number of matrimonial profiles, I am glad that I connected with you. Your approach towards tailoring my matrimonial profiles and search filters was pretty effective. I got matched with a good number of suitable prospects in a very short period of time. I also had meaningful, promising interactions with few of the matches. The comfort level and your attention to detail certainly stand out. Partner search can be overwhelming and exhausting in many ways and when you can entrust this job with someone who gets you, the relieving feeling is inexplicable.”

Cool Date Ideas

This isn’t so much a date idea as it is a proposition. When you go on a single date with someone, unless you got dead-bored, I’d encourage you to give it another chance. First dates are awkward, people are nervous, nobody knows what to expect but you can only tell if someone’s being nice or not. May be sometimes that’s good enough to meet them again.

Basic hygiene:

  • TURN ON VIDEO (didn’t think I’d be saying this, but yeah)

  • Dress up for the date.

  • Smile. Think about how beautiful this is that you get to meet someone new and interesting in the comfort of your home. So, just smile.

  • Rate your date right after, so you can another date.

My favourite date this week wasn’t the celebrity one, it was another date that resulted in two people wanting to meet again despite not rating each other very high on relevance. They spoke about lots of different things, they found each other interesting, and that was good enough to want to meet again. This was worth every minute of my time in bringing them together.

Humans of Dinner Club

As promised, I’ll pick a line from your forms each week that made me smile:

“I’ll tell you when we meet.”

Apart from being able to email me, all of you have 3 chances to help me learn about you - your bio, your quirks and your video. This apart, you can also leave detailed feedback on what you want or what you don’t want after each date, but if you still choose to be cryptic with me, unfortunately, there’s very little I can do to help make this experience more fruitful.

What’s up next week

  • The worst thing about most dating apps is that they contain a lot of dead weight - people who aren’t single anymore, people who signed up when drunk or people who’re not serious about dating at all. Anyone with an incomplete application (read no video), will stop receiving updates from Dinner Club from next week so I can focus all my energy on the ones who’ve actually made the effort to participate wholeheartedly.

  • I want more of you to experience Dinner Club dates, so I’ve opened up 12 slots a week (Thursday-Sunday). Here’s a tracker to input your availability so it helps me organize your dates more easily. I promise to not make you fill more forms.

  • I’m about to schedule 10 dates next week. Those who’ve dates lined up next week have already heard from me, and will receive invites by Monday. I’ve one free spot on Friday night at 9pm currently open. So, I want to try something interesting this time. I will pick two people who respond to this newsletter indicating an interest to meet in this slot, and send them on a date.

If you’d like to invite your friends to dinner club, share a link to the landing page…

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More from Dinner Club

Sharing things I’ve read, watched, listened to or written/ said myself:

How to be certain about a potential partner

What to talk about on a Date?