Introduction
Here at Sunday Singles, we’ve put together a list of some of the best conversation starters we’ve noticed at our shows that really help make a first impression. First of all, our focus is on a light-hearted approach, mixing humour into the questions. While having a sense of humour is great, it’s equally important to be able to hold a proper conversation. After all, it can be frustrating if someone can’t switch between a serious conversation and a funny one, which is why we’ve curated a balanced list for you.
When you meet someone, it’s important to stand out from the rest. Incorporating humour into your conversation will undoubtedly give you a head start, but you should still make sure to let the other person talk. In order to make it easier, we’ve broken the questions down into sections. So, take your pick and see how they go!
One final piece of advice: Ask questions that don’t require just a one-word answer like “Yes” or “No.” This way, you encourage the person in front of you to open up. Moreover, try not to talk about yourself too much. You need to find out if you’re compatible, and you won’t know this if you’re doing 90% of the talking. Therefore, share the conversation evenly, aiming for a 50/50 split.
Here Is Some Of The Best Speed Dating Questions
1. Light Hearted Speed Dating Questions
These questions are a great way to ease into the conversation and show some character. They’re different from the usual, “What’s your favourite colour” or “What do you do for work?” and help set you apart from everyone else.
- What’s something that everyone looks silly doing?
- If your pet could talk, what would they say about you?
- What’s the most embarrassing outfit you’ve ever worn?
- If you could travel to any place in the world for a month, where would you go
- Where’s the best place you’ve ever travelled to
- What’s something you’re superstitious about?
- What’s your go-to hangover cure?”
- What kinds of things do you find repulsive?
At Sunday Singles, these light-hearted questions are often the ones that break the ice during our singles event, which is a comedy dating game show for singles. They help kick off real conversations with a laugh!

2. Funny Speed Dating Questions
Once things are going well, you might want to step it up with some humour. These questions show that you’ve got more to offer than the typical conversation they’ve heard all evening.
- What would be the creepiest thing you could say while walking past a stranger?
- If you were arrested with no explanation, what would your friends assume you’d done?
- What’s something that’s really popular now, but in five years everyone will cringe at?
- If someone wanted to be your apprentice, what would you teach them?
- If you were transported 400 years into the past with nothing, how would you prove you’re from the future?
Humour is at the core of what we do at Sunday Singles. Our comedians help participants open up, creating an atmosphere of laughter and genuine connection.3. Meaningful Questions
These questions are perfect when you’re getting along well and think there’s potential. You don’t want to start with heavy topics, but eventually, these questions can help ensure you’re on the same page.
- “What are your top three rules for living?”
- “Do you have kids, or do you want kids in the future?”
- “What type of relationship are you looking for at the moment?”
- “Do you have any siblings?”
- “What do you do for work?”
3. Meaningful Questions
These questions are perfect when you’re getting along well and think there’s potential. You don’t want to start with heavy topics, but eventually, these questions can help ensure you’re on the same page.
- “What are your top three rules for living?”
- “Do you have kids, or do you want kids in the future?”
- “What type of relationship are you looking for at the moment?”
- “Do you have any siblings?”
- “What do you do for work?”
At Sunday Singles, we believe that creating genuine connections involves a balance of funny, light hearted and meaningful conversation. Our events give you the chance to dive deeper without feeling rushed or pressured.

4. Risky Speed Dating Questions
These questions can be a bit personal and should be used cautiously. Once you’ve gauged the other person’s comfort level, these could help you take the conversation further.
- “What’s the most important thing you’ve learnt from your last relationship?”
- “Are you an easy person to date?”
- “Should couples have separate or shared bank accounts?”
- “What area do you think you need to improve in a relationship?”
- “If you could change one thing about yourself, what would it be?”
- “What do you think happens after we die?”
- “What’s been your biggest mistake so far?”
- “What’s the biggest lie you’ve ever told?”
At Sunday Singles, we encourage open conversations, but we also believe in keeping things light. Laughter often makes even the riskiest questions easier to tackle!
Is There A Better Alternative to Speed Dating?
Speed dating might let you meet a lot of people quickly, however, it often feels repetitive, and there’s limited time to form real connections. This is why Sunday Singles does things differently. Our Comedy Dating Show mixes humour with interaction, therefore giving you a chance to meet people in a relaxed, pressure-free environment.
For example, imagine being in a comedy club, where comedians break the ice for you and laughter fills the room—creating a much more genuine connection than what you’d get from a timer ticking away in a speed dating setting. Rather than repeating the same questions again and again, you get to enjoy an entire night of fun, laughter, and organic conversations.
In conclusion, Sunday Singles is more than just meeting people; it’s about creating memorable experiences. Our shows feature Australia’s funniest comedians, which helps make the interactions relaxed and entertaining, ultimately allowing you to connect more naturally.








