Page views 49003

Sociability • Friendship

Virtual Dinners: Conversation Menus

We typically spend a lot of time getting the table and food right when we invite others over for a meal; but now that no direct hosting will be possible for a while, we have one small but central advantage. We can properly concentrate on the best bit: the conversation. We can invite others to a chat room at dinner time – and there talk as we’ve seldom done before.

Typically, we stumble on fascinating conversation topics a little bit by chance. Shyness can hold us back. We can fall back on polite but not especially inspired staples. That’s why it may be worth sharing a set of Virtual Conversation Menus with some friends ahead of time and then working our way through ‘imaginary courses’ during an online chat.

Arranged to accompany a virtual dinner party, these Conversation Menus invite us to open up around key themes: the virus, but also love, money, travel, ambition, self-knowledge and the meaning of life. They contain questions that will raise smiles, build friendships and foster the best kind of intimacy, ensuring that our meals apart can be as good as they ever were together.

Conversation Menu: The Virus

First Course

– What is it you most miss of the old world before?

– What will you do more of as soon as you are released?

– What is it you understand better now?

– What seems much less important now?

Main Course

– How could you best use your time in this period?

– What most reassures you?

– How would you calm down an anxious seven year old who came to you for advice?

– Who most inspires you in this period?


– Describe an ideal location you’d now like to be in if you could still travel?

– What kind of physical contact do you miss?

– If you had to write a book during this period, what might it be about?

– How do you hope the world could change for the better after this?

Conversation Menu: Ambition

First Course

– Were your parents fulfilled in their ambitions for themselves?

– What were your parents’ ambitions for you?

– What remains for you to achieve?

– Who would you like to impress?

Main Course

– What achievements of others make you jealous?

– What personal vulnerabilities and flaws have held you back in your ambitions?

– What, for you, is the relationship between lovability and achievement?

– What is failure for you?


– What alternative careers do you suspect you might be rather good at?

– What price have you paid for your ambitions?

– What is the best way to cope with the disapproval or neglect of the world?

– Knowing what you now know, how would you advise a very young person about their ambitions?

Conversation Menu: Love

First Course

– Finish this sentence: If someone likes me a lot, I start to feel…

– In what ways are people you are attracted to similar to one or other of your parents?

– On a date, what would you most want to be liked for?

– What kinds of suffering would you want a prospective partner to have experienced in the past?

Main Course

– In what way is your partner (or an ex) quite annoying?

– List five ways in which you are, after all, quite difficult to live with.

– In what ways are you not a great communicator?

– What’s tricky about sex?


– Are you good at breaking up? 

– Which of your ex-partners hurt you the most?

– Make a case for why adultery could, sometimes, be excused.

– Which of your flaws would you like to be treated more generously?

Conversation Menu: Self-Knowledge

First Course

– How much do you like yourself? What do you attribute this to?

– In what ways are you neurotic (given that we all are)?

– What difficulties did your childhood bequeath you?

– How might people describe you when you are not in the room?

Main Course

– What do you find it difficult to communicate directly?

– In what contexts do you find it hard to trust people?

– What do you characteristically do when you are emotionally hurt?

– In what areas of life would you describe yourself as immature?


– How did your mother leave you feeling about yourself? And your father?

– How do you typically respond to frustration?

– What do you think explains why you personally are more of an introvert – or an extrovert?

– How would you still like to grow emotionally?

Conversation Menu: The Meaning of Life

First Course

– What problem would you like to solve for other people?

– Name two meaningful moments you have had.

– What is a meaningful conversation in your eyes?

– How has your quest for a meaningful life made relationships and your career more meaningful but more difficult for you?

Main Course

Imagine you have five years left to live. Assume you won’t be incapacitated until the moment of death. What would you have the confidence to do – now that your death verdict has been announced – that you might previously have lacked?

– In my relationships, I would have the confidence to…  

– In my friendships, I would have the confidence to… 

– In my work, I would have the confidence to…

– With my family, I would have the confidence to…


– What’s the greatest unhappiness in your inter-personal life at the moment?
– What transcendent experiences have you had? Where were you? What did
they feel like?
– What sort of group could you imagine belonging to? What would it need to be
like for you to feel proud to belong?
– What advice would you give to your 19 year old self? How have you grown since then?

Conversation Menu: Secrets

First Course

– Tell your dinner companion a big secret about yourself.

– How do you secretly hope a friend would describe you at your funeral? Be as specific to your individual character as possible.

– What’s the worst thing you’ve ever done? Name the general area if the specifics are too tricky.

– What negative character flaws do you fear — in your worst nightmares — that other people have spotted about you?

Main Course

– List three things about a person close to you that secretly annoy you (like humming, doing the wrong thing in the bathroom, being late…)

– What sort of things have made you envious recently?

– List three (now guilt-inducing) occasions when you were especially mean to certain people.

–  What things would alarm your family if they knew?


– What are some of your most pervasive insecurities?

– What do you worry about in the early hours?

– What do you think is quite odd about you?

– Which of your flaws would you want to be forgiven?

Conversation Menu: Resolutions

First Course

– What immature side of yourself would you like to work on? (we all have them)

– Describe one thing you would do in the coming 12 months if you were a more confident person.

– If you could not fail, what would be the ideal next move in your career? 

– Who are you envious of? What positive bit of their life can you introduce into your own?

Main Course

– Describe your life in the most boosterish, optimistic way. Then in the darkest, most honest, most pessimistic way.

– How did your parents shape what success and failure mean to you? 

– What old ambition can you happily let go, knowing you will never achieve it? 

– What can you forgive yourself for? What could you forgive another person you know for? 


– Who in your life can you draw supportive energy from to realise an ambition? And who drains your energy – who might you have to let go?

– What small evolutionary steps – a daily practice or good habit – could you undertake to realise an ambition? 

– If this was the last year of your life, how would your resolution change?

– How do you hope your life will look different as a result of a resolution – in a year’s time?

Conversation Menu: Family

First Course

– What do you blame your parents for?

– What do you credit your parents for?

– What might a good friend of your parents say about their inadequacies?

– What did you learn about relationships from your parents? What have you tried to unlearn?

Main Course

– What was once rather sweet about you?

– What qualities did you possess as a child that you wish you still had more of as an adult?

– Have you ever had an imaginary friend or very favourite soft toy? Describe them.

– What were you especially embarrassed about as a teenager?


– If you had to join someone else’s family, what sort would it be (design the ideal one)? 

– In what ways are you envious of your siblings? (If you do not have siblings, choose other relations of your own generation.)

– Of the family you spend time with, who brings out your best qualities?

– What three things do you enjoy doing most as a family? And least?

Conversation Menu: Hope

First Course

– What’s the kindest thing anyone’s done for you?

– Describe an important teacher in your life – outside school.

– Name something nice that happened to you today.

– What small everyday pleasure do you love?

Main Course

– What is the most significant difference you feel you have made in the life of any individual?
– Who has most influenced you in relation to wanting to make a difference? Tell us one person who you personally know, and one who is famous or historical.
– What would you change as the absolute ruler of the world?

– What small political change do you think you could help with?


– Misery likes company: what sad sides of yourself would you like to share if you could find fellow sufferers?

– What do you feel sad or anxious about on Sunday evenings?

– What message should the hopeful you more regularly impart to the despairing you?

– What do you remain hopeful about?

Conversation Menu: Work

First Course

– If I was more of a success, a/my partner would…

– If I was more of a failure, a/my partner would…

– Men secretly feel that successful women are…
Women secretly feel that successful men are…

– Could you respect a partner who earned far less than you? How would you feel if your partner earned far more than you?

Second Course

– What is the most cynical thing you could say about your work?

– In what ways is your organisation (a bit) dysfunctional?

– Ideally, my colleagues would be more like me. Discuss.

– The best person I ever worked for/with was so good because…


– When I was a child and thought about the future;  I wanted to be…

– If life were 400 years long, what careers would you want to have had?

– My ideal obituary would explain that I…

– You hear of someone who has died. Which of these are you most impressed to learn about their legacy and why?
a) They made a small contribution to a big project that was genuinely worthwhile.
b) They took honourable risks, quite a few of which didn’t work out.
c) They put family before maximising income.
d) They were a supportive colleague and mentor. 

e) They helped their partner succeed in their career.

Conversation Menu: Confessions

First Course

– Which of your exes would you like to go back and sleep with?
– What do you wish your partner could forgive you for?
– How has your childhood made you difficult to be around?
– What mistakes would you want to avoid in a future relationship?

Main Course

– Describe your discovery of masturbation.
– What hang-ups do you have around sex?
– What part of your body do you worry might put a lover off?
– What do you want more of in your sex life – but have difficulty asking for or finding?


– How much do you earn? 

– What would you fix in your life with infinite money?
– What salary level for another person starts to make you feel humiliated at your earnings?
– What is it about your character that hasn’t enabled you to make more money?

Conversation Menu: Taboos

First Course

– Are you dominant or submissive sexually? And in the rest of life?

– Have you ever had an incestuous thought? Who was it about?

– Name three sexual scenarios that especially excite you.

– What experience do you have of impotence – yours or a lover’s or a friend’s?

Second Course

– How much money do you have in your bank account? 

– What would be the first thing you would do if you won the lottery? 

– What do you, perhaps secretly, spend really quite a lot of money on?

– Which of your acquaintances/friends/family members makes you feel inadequate around money?


– When was the last time you experienced ‘Schadenfreude’? Do you dare to admit what triggered it? 

– When have you acted without 100% integrity?

– Have you ever sabotaged your own success?

– Which close relative do you like the least – and why?

Conversation Menu: The Body

First Course

– What about your body is desirable?

– In what ways has your physical appearance affected your personality?

– If you could redesign your body from scratch, what would it look like?

– When you look in the mirror, what’s the first thing you check? 

Main Course

– What do you find physically attractive in others?

– Give the person you are talking to a sincere compliment about their physical appearance. 

– What repels you in other bodies?

– What clothes interest/excite you, for yourself or others?


– What elements of physically ageing are your most afraid of or upset by? 

– What might be the upsides of ageing?

– How have you been aging recently? What do you notice?

– At the current rate, what might  you regret on your deathbed?

Conversation Menu: Utopia

First Course

– In a better society, what would people be like? Describe their (psychological) characteristics?

– How would you like to be a better person?

– If you had magical powers to ‘improve’ two people around you, what would you correct in them?

– What are you oddly, perhaps privately, remarkably utopian about? What do you allow yourself to be idealistic about?

Main Course

– Design your ideal country: how would it be different from your own?

– In your utopia, what would be banned?

– In your utopia, who or what would be more readily forgiven?

– In the utopia, everyone would try out four very different careers in a working life. What would you pick?


– In your utopia, who would deserve to be treated as a celebrity? 

– In the utopia, education is a lifelong endeavour. Schools and universities teach their students not just formal knowledge, but the emotional skills they need to thrive. What subject or lesson could you teach?

– In the utopia, advertising does not promote useless things, but virtues and good causes. What would you like to advertise? 

– What can you do to make the world a slightly better place?

Conversation Menu: School

First Course

– What’s it taken you a bit too long to learn about yourself?

– What would you want to teach your younger you about life?

– Name a psychological area in which you are improving as a person.

– If you had the patience and opportunity, what would you ideally want to teach a family member about life?

Main Course

– How did you suffer at school?

– What was, in a way, fun at school?

– Who did you have a crush on during your school years?

– Who did you dislike at school? Why – with hindsight – do you think that was?


– In your ideal school, what would people be taught?

– What would you, ideally, want to teach people about love?

– What should young people learn about the world of work?

– How would you like to be a wiser person going forward?

Conversation Menu: Travel

First Course

– Describe your first memorable encounter with another culture.

– What for you counts as ‘exotic’?

– In what ways are you not a good traveller?

– What supposedly interesting destinations do you have no interesting in seeing, and why might this be?

Second Course

– With a citizen from what country other than your own could you imagine having a fulfilling relationship? What might you learn?

– Describe, in some detail, your ideal hotel.

– What do you still want to discover in the world?

– What occupation or role would you be well suited to if you could travel back in time to another era?


– Describe an ideal travelling companion.

– What sides of you does your own country not understand/enhance/reflect?

– When you say you are interested in ‘other cultures’, what bits specifically interest you?

– What images/sensations/moments of trips have stayed with you? Be precise and evocative.

Conversation Menu: Children

First Course

– What is the point, if any, of having a child?

– In so far as you find children endearing, what is it that moves you about them?

– In what ways are children a disappointment?

– How do children spoil the relationships of their parents? And enhance them?

Second Course

– Describe an ideal (not perfect, just ideal for you) child, in your eyes, according to your values.

– What mistakes do you feel many parents make?

– What should children learn about the adult world?

– How might you (inadvertently) mess up your children?


– What might a child find ridiculous about you?

– What might a child find endearing/charming about you?

– Where do you lose your temper with children – and why might this be?

– What have you ever learnt from a child?

Conversation Menu: Friendship

First Course

– What sides of you still feel lonely?

– Describe an ideal, imaginary friend.

– What frustrates you about social life?

– What would help to turn a stranger into a friend? 

Second Course

– When you are made anxious by being in company, what are you anxious about?

– What do you want your friends to ‘get’ about you?

– What enables you to ‘connect’ well with someone?

– Who have you had to eject from your social life – and why?


– What would you want to admit to a true good friend?

– What would you want to laugh about with a true good friend?

– ‘Every time a friend of mine succeeds, a small part of me dies,’ said Gore Vidal. What does this make you think of in your life?

– Tell a companion at table something vulnerable and revealing which opens a door to deeper friendship.

Conversation Menu: Death

First Course

– What would you ideally like to tell someone you once knew who is now dead?

– What must you remember to tell someone before they die?

– Who you are afraid of not feeling the ‘right’ things around when they die?

– Whose death would you find almost impossible to get over?

Second Course

– What part of your body do you suspect is going to let you down fatally in the end?

– What do you still need to do before you die?

– How many summers do you guess you have left?

– Imagine giving an address at the funeral of someone around the table: what would you say?


– How would you like to be remembered?

– What is liberating in the idea of death? What might it be a relief from?

– Knowing we are all dying (at varying speeds), what honest, direct thing would you like to tell your companions at this point? Make a short speech if necessary.

– What would you like the idea of death to liberate you from?

Conversation Menu: Money

First Course

– What feels like enough money for someone to have a year?

– What is a noble way to make money?

– In what ways are you somewhat irrational around money?

– What are you ashamed of around money?

Second Course

– How might money corrupt you?

– What would you do with unlimited funds?

– What sides of your character have stopped you from making more money?

– What suspicions do you have of the very rich? And the very poor?


– What would you want to teach a child about money?

– What shaped your attitudes to money?

– What role has money played in your relationships?

– How, in your mind, are money and sex connected? Why are both often very taboo?

Conversation Menu: Culture

First Course

– What would you like a book to explain to you?

– If you were to write a book, what might it be like and about?

– If someone were to make a film of (bits of) your life, what might be key elements of the plot?

– What has shaped your taste in interior decoration?

Second Course

– In what areas do you feel you might have ‘bad taste’?

– What supposedly great art is not for you?

– In what ways, and when, have you been dishonest about your cultural tastes and dispositions?

– What kind of tastes in art would an ideal lover have?


– Shared embarrassment brings people closer: hum one of your favourite songs to a dinner companion. Listen to them do likewise.

– Write the first sentence to an imaginary book which you’d want to keep reading thereafter.

– If you were a great visual artist, what elements would you want to bring out in a dinner companion?

– With a companion, sketch the plot of a thriller you could write together: what might happen in it?

Full Article Index


Get all of The School of Life in your pocket on the web and in the app with your The School of Life Subscription