Dinner Club#6: Opposites don’t attract

Hello Dinner Club fam,

Like you, I believe in serendipity too. As you know, Dinner Club was started on a whim, and I’d planned to take 3 months off my main gig, M.B.A. (which had become quieter, thanks to covid) to pursue a fun side-project. I don’t know if it’s all the good karma from setting some of you up, I got featured by the Times of India in their article about new age matchmakers. A lot more exciting things have happened, but not something I can share just as yet. But I’ll say this…

Thank you for all the good karma you guys have brought me.

As all good things must come to an end, so did the applications for Dinner Club. Yesterday, the sign up button on Dinner Club was taken down, and in its place is now a “Register” your interest button. I figured that closing applications a month before the end of the project would truly allow me to do justice to most of you who’ve signed up. But turns out scarcity is exciting. Who knew?

About this week

I may have taken too much risk this week by pairing seemingly opposite personalities to see if sparks fly. Turns out opposites don’t always attract. There have been far fewer double opt-ins this week. Some of you have been great sports in saying, “hey, this didn’t work, but that’s ok, that’s what makes this experiment fun” while fewer others said “no, thanks”. So much for serendipity.

Here’s what some had to say:

Wavelengths didn't match to a large extent.

He seemed genuine and I felt really comfortable to talk to him.

Nothing particularly stood out.

Conversations were open, authentic and warm.

Sometimes I wonder if human+tech works better than just human or just tech. In order to experiment with the matching while still keeping a human element, I thought of three ways to do it:

  1. Wet algo generated matches

  2. Replicate me/ have more matchmakers

  3. Crowdsource matching to you guys

These are all just random musings at this point, but I will continue to do what I do for the rest of this month. If any of you have thoughts on the ideas above, drop me a note.

Tell me what you think


  • Dating app fatigue is a thing. Turns out going on too many dates is just as tiring as not being able to go on enough depending on who you are? Who knew?

  • Manually tabulating social credits is a nightmare, and hopefully I can find a fully automated solution if I were to do this again. Anyway, I will be sharing social credit information with those of you who’ve got less than 5 points, which means you cannot go on any more dates/ events. :(

  • While reviewing all the feedback I’ve got so far, I noticed an interesting pattern. Most people who said something to the effect of “I liked that the other person was listening to me and engaging me by asking questions” did not end up getting a second date with the same person. You may be an introvert, but if you display a lack of curiosity, the other person may not enjoy the date as much as you. Conversations are two-way.

  • I was having a conversation with a friend earlier this week where he challenged my hypothesis about serendipity and blind dates stating that people enjoy more control. However, I’ve seen mixed reaction from this group, and it is quite strongly correlated with age. Interesting, huh?

Cool Date Ideas

While I got interesting ideas from the crowdsourcing experiment, I couldn’t really set anyone up amongst those I received feedback from since it was mostly from one gender, and they were all heterosexual. Nevertheless, I’d like to share 3 ice-breakers from the ones I received. So feel free to use them if you like.

  • What made you try Dinner Club?

  • What would you be doing right now if you didn’t have this date?

  • Each one brings a 5min game to try with the other.

What’s up next week?

  • Some of you will finally go on your first dates. You’ll hear from me soon. Yay!

  • We have the “Assessing Your League” workshop, for which registrations are now closed, thanks to the overwhelming response.

  • I’ll start planning the following events that are due later this month:

  1. Brainstorm: Dating Apps of the future

  2. Story Collective: Singledom & Dating

  3. Speed-Dating (woohoo!)

  • If you’ve friends who couldn’t be a part of this experiment, but would like to be in the future, you can share the link below so they can “register” their interest.

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