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Conversation Starters: For when "how are you?" just isn't cutting it

With Covid-19 and our lockdowns around the world, whether it’s family, friends or work colleagues. Keeping conversation with these people is important for our mental health. But speaking from experience running my team meetings and also dating someone new during this madness, it’s difficult to think of topics to discuss.

I mean, “How are you?”, “How was your day?” – really, well it was the same as yesterday, worked, ate, watched TV, drank, slept and woke to repeat. Nothing exciting is going to happen, talking about Covid-19 is vetoed in my group of friends. What the hell are we going to talk about??

Here are some questions that thought would be good to share with you, that you could either text in a group message, asking in team meetings to get to know people. Or if you are starting on the dating game, and unable to meet with your new match, try some of these questions to get to know someone.

Here are some top tips on having a conversation, it’s not just the topics you need to be aware of and have ready.


Yep, actually listening to the person and their responses. Nowadays we are thinking about the ironing we have piled up to complete, or we look at an area in our home and we think to ourselves, need to sort this out. We tend to listen to respond rather than listen to understand. Active listening includes hearing what the other person says, with empathy, understanding and maybe follow on questions to their answers. Remove all distractions, turn the TV off, put the laptop away (unless you’re on zoom), pay attention to the words used and tones. It means a lot to someone that you take the time to do this.


Not one of my best qualities but sometimes I’m so excited about a topic and/or want to say something before the thought goes out of my mind (like the dog in the film Up – when he thinks he sees a squirrel). You may not also know this, but it’s seen as a form of domination (not the world), but it’s away of asserting your point of view. Which I get, there is a time and a place, but if it’s because like me you’re super excited or about to forget what you are going to say, there’s nothing wrong with having a pad and a pen with you to remind you of what you wanted to say when the person you are speaking to has had their say.


Some of the questions below might start a great conversation, you get a good rally going and you have a laugh and a joke. Some of the questions may open up wounds or start conversations down a heavy route, if this is the case, again just listen. Sometimes people don’t want the solution or what you think is a solution to the problem. It’s ok to say, “That sucks”, or ask, did you want my opinion or just someone to vent to. Giving the option will allow that person to feel that you there for them, not to press your thoughts onto their life experiences.


Having a conversation with someone, they may say something that hurts you or make you feel feelings that you didn’t want to. It may be that communicating with someone, they take your words out of context, or visa versa. Simon Sinek has a great method of explaining how to be open with someone and you can do this at work, at home with your kids or partner. Can foster a structured format and not put fuel on the fire, rather than raising your voice or just getting pissed off. The technique is called FBI – I know, I know, but it stands for Feelings, Behavior and Impact. The order doesn’t matter, you must be specific. Using phrases like I’m not happy, sad or annoyed, and the impact you used, isn’t “because something bad will happen”. If you are not specific that person can challenge and confront you back.

I’ll give you an example:

Someone is late for meetings (workplace example)

Wrong: You can’t keep turning up for meetings late, as something bad will happen.

Suggestion: When you turned up for the meeting on Thursday and you are late, this impacts the team as they are frustrated, and I feel you are wasting time and it comes across like you are not bothered about this topic/subject, I’m concerned that the rest of the team will not be motivated on the project.

Then stop! If they come back with a rebuttal just repeat your sentence.

Walked out of the room on Thursday after we had a heated discussion with the kids (home example)

Wrong: You really annoyed me and upset me when you walked out of the room the other day you just don’t care.

Suggestion: Remember when we were having a heated discussion with the kids and you got up and walked away as it appeared you couldn’t be bothered to continue the conversation and resolve this, I fear that the kids could see we were not aligned and that in the future we will attempt to discipline them in different ways. Plus, it made me wonder if you were going to support in the future with this as I need a partner to support me.

Then stop! If they respond with “well the kids were doing my head in, I’d had a long day at work”, maybe say I understand that, but just repeat it again.

This process allows the other person you are speaking to, understand and hear what you are going through.

I also have included at the bottom, some questions to ask if you’ve been in a relationship for years and want to know more about your partner – other than, have you done the bins, taking turns in helping with the math’s homework, as I did science yesterday.

Disclaimer: Please note that if you ask these questions to a loved one, be prepared for different answers than you may expect, and it may change the perception or your feelings towards someone. I note as this has happened to me in the past and it’s made or broken a relationship.

Fun Questions:

  • If your house was burning what would be the first thing you would save?

  • If you won, the lottery what would be the first 3 things you'd buy?

  • Do you have any tattoos?

  • If you could invite 3 people from the past or present to dinner who would they be and why?

  • When was the last time you cried and why?

  • Who do u admire and why?

  • What's your earliest childhood memory?

  • What would be your dream job?

  • What's your biggest regret?

  • What thing are you most proud of?

  • What would you do if had enough money to not need a job?

  • What was the last show you binge-watched?

  • What TV series do you keep coming back to and re-watching?

  • What hobbies would you like to get into if you had the time and money?

  • If there was an Olympics for everyday activities, what activity would you have a good chance at winning a medal in?

  • what would your perfect vacation look like?

  • Among your friends, what are you best known for?

  • What’s your favourite app on your phone?

  • Cutest animal? Ugliest animal?

  • Who is the kindest person you know?

  • Where’s the strangest place you’ve ever been?

  • What’s the silliest fear you have?

  • What would be the best city to live in?

  • What household chore is just the worst?

  • What odd talent do you have?

  • What would you tell your younger self?

  • How did you meet your best friend?

  • What are you most grateful for?

  • What’s the most interesting fact, you know?

  • What skill or ability have you always wanted to learn?

  • Have you met any celebs?

  • What did you want to be when you were little?

  • What small things brighten up your day when they happen?

  • What’s the most spontaneous thing you’ve done?

  • What’s your go-to funny story?

  • Who the one person in the world that knows you the best?

  • What's your favourite quality in a friend?

  • Would you rather have the power to travel back in time or be able to see into the future?

Life Questions

  • Would you like to be famous? In what way?

  • If you were able to live to the age of 90 and retain either the mind or body of a 30-year old for the last 60 years of your life, which would you choose?

  • If you could wake up tomorrow having gained one quality or ability, what would it be?

  • If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

  • Is there something that you’ve dreamt of doing for a long time? Why haven’t you done it?

  • If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

  • Do you believe everything happens for a reason, or do we just find reasons after things happen?

  • Is there anything you consider absolutely unforgivable?

  • If you woke up tomorrow with no fear, what would you do first?

  • In your life, what has been the biggest blessing in disguise?

  • What is one behaviour that you never tolerate?

  • If you could write a note to your younger self, what would you say in only three words?

  • Who would play you in a movie about your life?

  • Do you believe in soul mates?

  • If you could pass one of your attributes to your kids what would it be and why?

  • If you close your eyes and think of 3 things that make you smile, what would they be?

  • If you could be a Disney or film villain who would it be?

  • If you bought a yacht and had to name it after me what would it be called?

  • What's the one thing you want to be remembered for?

  • What’s something you’re glad you’ll never have to do again?

  • What’s one thing you always procrastinate on?

  • What is the one thing that makes you feel alive?

  • What would your perfect day look like?

  • Do you usually follow your head or your heart when making decisions?

  • What is something that never ends well?

  • Where do you see yourself in 5 years?

  • Where do you see yourself living when you retire?

  • What are your financial priorities and goals?

  • What is on your bucket list that we can do together this year?

  • What’s the one thing you want to achieve the most before you die?

  • Do you have any habits you want to change?

  • What do you most look forward to about getting old?

  • When’s the last time you felt vulnerable? How did you cope?

  • What have you accomplished in the past year that you are most proud of?

  • What were the major turning points in your life?

  • When’s the last time you pushed out of your comfort zone? How did it make you feel?

  • What is your happiest memory?

  • How have you changed in the past 5 years?

  • What is an important life lesson you’ve learned?

  • What’s the most daring thing you’ve ever done?

  • What’s the most challenging setback you’ve ever experienced? How did you overcome it? 

Relationship Questions

  • What did you think when you first met me?

  • What about our relationship makes you really happy?

  • If you had one word to describe our relationship what would it be?

  • What’s your biggest fear for this relationship?

  • What’s one difference between us that you absolutely love?

  • What’s one similarity between us that you absolutely love?

  • What about me made you fall in love?

  • What’s your favourite memory of us?

  • What’s one thing you want to do together that we’ve never done before?

  • Where is your favourite place to be with me?

  • What’s one thing you’re scared to ask me, but really want to know the answer to?

  • What’s one thing you feel our relationship is lacking?

  • What’s your favourite non-physical quality about me?

  • If our relationship ended, what’s the one thing about it you’d miss the most?

  • What do you think was your most vulnerable moment in our relationship?

  • What’s one secret you’ve wanted to tell me, but haven’t?

  • What’s your favourite way to receive affection?

  • What’s one thing you think makes our relationship unique from everyone else’s?

  • If you could change one thing about our relationship what would it be?

  • What do you think is your biggest strength in this relationship?

  • What’s one thing about your life you would never change for someone else, including me?

  • What about us do you think works well together? How do we balance each other out?

  • What does love mean to you?

  • What do I mean to you?

  • Share with your partner an embarrassing moment in your life.

  • What are your goals in the relationship?

  • What is the biggest lesson you’ve learned from previous relationships?

  • What are your thoughts on having a family?

Some R rated ones:

  • Where is the most adventurous place you have done it?

  • Do you like being teased?

  • Where is your favourite spot to be kissed?

  • How do you feel about kissing in public?

  • What is one thing that gives you butterflies?

  • Using three words, how would you describe me?

  • What is your favourite thing about my body?

  • Do you have any secret fantasies?

  • What are some dreams you’ve had about me?

  • What is your favourite position?

  • Where do you like to be kissed the most?

  • If you were to give me a pet name, what would it be?

Hope you have fun with these questions and it gets the conversation started, when it's a little dry and samey.

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Snodland, Kent


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