Dating games

Ideas to ignite and sustain conversations with your date

This week’s theme is inspired by real attempts to ignite and sustain interest in conversations with prospective partners either in the same time-zone or not. Having said that, there’s no reason why seasoned couples who’re long distance must not try this.


I saw this on Twitter the other day, and I totally did get her sentiment. I’d really like to just get on with life, except it’s so bloody hard. I mean, corona just feels like a family member now, how can you not talk about it? No?

Our lives have changed irreversibly, and respite doesn’t seem to be in sight. Some of us are sick of all the social distancing, while few others are too anxious to enjoy it. Some of us are working more than ever, while others don’t have jobs anymore. Some of us are craving for company, while others for some time alone. The novelty of it all is starting to fade, and fatigue has surely started setting in. It’s hard to be optimistic despite our best efforts. In fact, it’s hard to even make any effort.

Sustaining existing relationships through this time is bloody hard, but starting new ones are even harder. I really feel for single people who entered the market just before lockdown with the best of intentions, but they’re now left to deal with the fatigue of the market. I’ve heard friends complaining about lots of things - Fewer match to conversation conversions, more ghosting, more fizzling, premature endings, one too many new beginnings and over-all far higher levels of maturity for anyone to be remotely excited. All of this is best captured in a tweet someone sent me:

But all the pessimism aside, I still get asked for ideas on how to keep the conversation going through the lockdown. So, I’ve put together a list of virtual dating games to keep the conversation and excitement at an optimal level as if the lockdown weren’t an issue, assuming you’ve the emotional capacity for this. Those of you who are in the market, try it and tell me ok?

  1. Date Night.

    For whom: If you hate texting, and you’d much go meet someone for a drink to get to know them.

    The game: Pick a date and time, decide where you’d like to meet - cafe, bar or a restaurant, dress up, set your table up with your food/ drink and your laptop in the comfort of your own home, pretend like your screens weren’t separating the two of you, and have a wonderful date. A bit crazy, you think? Yeah, but the kind of crazy you can fall in love with.

    Risks: If you’ve been in conversation with someone for a while and this isn’t the first time you’re talking face to face, this is a very low risk strategy with no downside, really. However, if this is your first ever date, and that too after very little initial conversation, then it’s slightly high risk, for which the pay-off can be pretty high. To limit your downside, coffee over video is the safest choice. ;)

  2. A question a day.

    For whom: If you are a compulsive text-er and enjoy long text conversations but you’re not sure if the other person enjoys chatting that much.

    The game: While the lockdown is exactly where long text conversations can be enjoyed, you might be left wanting more at the cost of annoying the hell out of the other person. So, to be safe, you could decide that you will each ask the other one at most one question a day. That’s it. If you’re struggling to figure out what questions to ask, I’ve something for you.

    Question Bank

    Risks: Minimal. You can keep people hooked without the risk of annoying them, and this also makes it rather clear if someone isn’t able to make time to answer even one question a day. Consider playing this only on weekdays to give each other some time to think of useful questions to ask.

  3. Food preferences

    For whom: Foodies (which is 90% of Indian men, at least according to their bios), and anyone who feels that their partner’s food preferences have an influence on the quality of your relationship with them.

    The game: Whether you do this on text or on an audio/ video call, pick a cuisine - either your favourite or the other person’s and then pick any restaurant you’d have liked to go to if not under lockdown, and then discuss the order that you’d like to place. This will generate lots of laughs or cries depending on how much your tastes interfere.

    Risks: You might just discover that despite the spectacular CV match, the two of you simply cannot find much common ground when it comes to food, and that might just be a deal breaker. Well, so be it. Food is a daily ritual and it’s fairly important for some people.

  4. Movie Marathon

    For whom: Self-proclaimed movie buffs who’d have loved to go catch a movie if that was an option. Remember that if going to a movie is your idea of a date, that means, you’ve definitely got the initial conversation out of the way because you can’t possibly talk much during a movie anyway.

    The game: This is a super silly but fun game to help break the ice, and also helps you figure out each other’s tastes in movies. This is best done over a video call. Imagine you are in the other person’s apartment for a date, so get into your comfy-est clothes, even pyjamas if you like and sit in front of your laptop with a piece of paper, a pen/ pencil and a timer. You say start, and your partner starts reciting A,B,C,D…in their mind and when you say stop, they tell you the alphabet they were at. This is exactly how you’d do with the game “Name-Place-Animal-Thing”. You both have 2minutes to list as many movies as you can from the alphabet you ended up with. Then you run each other through your lists eliminating all the common movies from both your lists, and then adding up the remaining movies. The one with the highest number of non-overlapping movies wins. You can play a best of 3 or 5 rounds. Simple, no?

    Risks: You might get bored if one of you is not into movies as much as the other, but otherwise, it’s pretty fun and addictive, mind you.

  5. Cooking together

    For whom: People who aren’t complete novices in the kitchen and wouldn’t mind getting cooking out of the way while talking to a date or the other way around.

    The game: Find a super simple recipe online, and cook a meal together. Either stay on an audio call or a video call while cooking so you guys can pretend like you are together while still social distancing. You can talk about food, or other things and you’ll discover things that you wouldn’t do otherwise if on a regular date. There are tonnes of amazing home cooks on insta that keep posting simple recipes. Here’s one that I’d highly recommend, for instance.

    Meal recipes

    Risks: You might be terrible at multi-tasking and the other person might find out sooner than necessary, or you might have a very untidy kitchen that you might be judged on, or you might sweat so much while cooking that you turn off the other person, but that apart, I can’t think of too many downsides.

  6. Online scrabble

    For whom: If you enjoy some intellectual stimulation, and want to do something other than just talking.

    The game: Find a good online scrabble game and play for a few minutes. The words you make could be suggestive. It could give you a clue into how the other person thinks, or it could just be fun. Actually this could be any game that you can play online - Chess, Poker, etc.

    Risks: You could easily get bored if you aren’t too engaged in the game or are distracted. The same thing could happen to the other person as it’s not talking to each other, but some people may enjoy it. This is definitely one of those high risk games, with a high pay-off.

  7. Stalking the market

    For whom: Only the crazies.

    The game: Get on a video call, and help each other pick prospective partners on one of these popular matrimonial sites like or via screen share. You can gossip about the things people write on their profiles and preferences, including your own. This will be insanely weird, yet fun and will help you get to know the other really well.

    Risks: You’ll get friend zoned. The upside is it’s unlikely’ you’ll get ghosted because now you know the worst things about each other. Again, yet another one of those massively high risk games with insanely high pay-off. You might very well be rejected for even suggesting this in the first place but remember if you were convinced enough to pop the question, this could be viewed as a self-elimination strategy.

These are just a few ideas that have been tried by a few including myself, and found to be quite fun, if not anything. But if it backfires, you know where to hit unsubscribe now, don’t you?

Projects from Shapely Gal

As mentioned in my previous few newsletters, there are a few initiatives that I’ve been working on with a few friends that I’d like to remind you about in case you haven’t had a chance to participate or share with those who might find this super relevant.

  1. Couples in Lockdown- Sustaining relationships through the lockdown ain’t easy, so we @loveinlockdown are featuring couples who are keeping it together in a series called “Couples in Lockdown”. If you are one of them or happen to know one of them, write in with a story and a picture so you can help inspire others who are clearly running out of ideas to last them the lockdown.

  2. Ghost Stories- This is an initiative to allow people to talk about their experiences of ghosting or being ghosted without judgement. Although being ghosted is so common nowadays, the experience remains fairly unexplored. This project aims to put words to your experiences of being ghosted so you can acknowledge and move on. If you’ve a story to share…

    File away

  3. How to attract the right partner in 30 days - Remember the course I built for Masterlife to help people understand how their personality influences their choice of a partner? I’ve been getting some very useful feedback from friends who’ve signed up. If anyone wants to top up their courses with a session to discuss their insights with me, I’m happy to do so. Giving away upto 3 free sessions (worth Rs. 2,500 each) this month.

    Sign Up

  4. Relationship Coaching- Over the last 4 years, I’ve been advising people who are looking to get married through M.B.A. Recently, I’ve realised that the methodology I use, can be applied to a much wider audience across age groups and at different stages of a relationship - single, married, straight, or not, monogamous, or not, casually dating, divorced, confused, whatever. If you’ve enjoyed reading what I write and you have a relationship question/ issue you’d like to discuss, drop me a note to schedule a session with me as I’m offering upto 5 free sessions this month.

    Reach out!

    Sneak peak into …

    What I’m reading:

    • Daring Greatly - Brene Brown - I’m halfway through this book and I’ve found myself sobbing from self-awareness several times.

    • Modern Love - In case you guys didn’t know already, NYT subscription is at Rs.25/ week now. So hurry if you haven’t already bought yourself a subscription because this column is one of my favourites.

    • Esther Perel - As some of you already know, I’ve been obsessing about self-love, and I stumbled upon this piece of gem.

    And what I’m listening to/ watching: Honestly, I’ve no time to sit and listen to/ watch anything productive anymore. But if you insist, here goes:

    • Ramayan (kidding!)

    • Karan Johar movies (not kidding)

    • Tonnes of videos on School of Life.

    Shapely Gal is a weekly-ish newsletter that discusses love, relationships, marriage and the various markets these are traded on. This newsletter is a concoction of observations, theories, ideas, real stories, figments of imagination and sometimes just rants on romantic relationships.