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55 Best Would You Rather Questions To Spice Up Your Speed Dating Game

55 Best Would You Rather Questions To Spice Up Your Speed Dating Game

So you’ve finally made a decision to get back on the dating scene. You’ve even made it your personal responsibility to tick all the boxes on the potential date checklist. But there is one thing missing in your carefully thought out plan- “What the heck are you going to say to a total stranger”. No need topanic, we’ve got you covered. In this article, we’ll outline the ‘best would you rather questions’ to help you initiate an engaging conversation with someone you just met.

What are ‘would you rather questions’?

As the name implies, it is a unique and interesting way to get to know another person by asking “would you rather” followed by a question. This conversation technique is one of the best ways to get to know people. This playful task requires the person you are speaking with to choose between two alternatives, which are usually between two opposing options. Would you rather questions are a sure-fire way to know people and provoke interesting conversations. It can be played between just two people or within a group.

When you meet people, to avoid moping into the junket, you would need to have a conversation to get to know them because;

● Small talk might get boring, talking about yourself might come off as being too self-absorbed,
● Current affairs, depending on the trends currently making the rounds, might be more of a conversation

terminatant rather than initiators or even facilitators for that matter.

● And merely making conversations for the sake of politeness could come off as bland. Or simply not having anything interesting to say, which will most likely disrupt any further conversation.

With this in mind, you have to be prepared. Learn several conversational tactics to keep your chat flowing. Especially if it is in a non-physical settings, like an online or otherwise.

Some examples of ‘would you rather’ questions

● “Would you rather ride a donkey or a giraffe as your only mode of transportation?”

A question like this could be a great way to follow up an initial conversation. It is quite funny, given the leaps and bounds manufacturers have made in automobile technology. Wouldn’t you like to know what they’ll chose ? Donkey or Giraffe? One looks cool and very impractical, while the other is not so cool but is indeed practical.

When you’re on a date, it’s better to start a conversation with a little humor. Being able to elicit a smile or laugh from your date goes a long way to ease that awkward first-meet tensions and/or silences. It also helps to put a gauge on their sense of humor. This could act as a guide in taking the conversation further and most people consider it a criteria when rating the outcome of any date. Are you too serious or too silly?

Follow up questions

After accessing you date’s reaction to your opening joke, you could take it a step further with more funny would you rather questions like

● “Would you rather your farts call out your name or your sneezes call out your name?” or
● “Would you rather forget the names of your relatives or forget their addresses and homes?”.

Immediately you break the proverbial ice with a bit of humor, the date is now past the introduction phase; you can then move on to flirtier, romantic territory.

Flirty “would you rather” questions

When getting to know each other, a bit of flirting could be fun. It could also be a way to open the conversation to broader topics.

● “Would you rather gaze at the stars or at gaze at your partner” or
● “Would you rather get a hug or just cuddle?”

Questions like this helps to guide the conversation toward a flirtier territory. You can guesstimate just how into you your date is or isn’t. You could go further with follow-ups like;

● “Would you rather have a back massage or foot massage?” or
● “Would you rather dance to slow music or go wild to popular music?”.

Depending on your date’s response, you could take things up a notch to more romantic realms or temper things down with something more thought-provoking.

Intellectual would you rather

Should you decide to take the conversation towards a more intellectual direction, you can pick your date’s brain a bit. You could ask would you rather questions that get people thinking. Like;

● “Would you rather be feared or loved?”
● “Would you rather tell the uncomfortable truth or tell a comforting lie?”
● “Would you rather travel to the past or travel to the future?”

These questions will make you and your date think about old concepts in a new light and hopefully get each other to open up even more about yourselves. If your date’s intellect is a priority, their responses to these “would you rather” questions will paint you a good picture. This a good conversation tool for those that like thought-provoking discussions and could facilitate lasting bonds during your date.

Reviving would you rather

In the unlikely event that during the date, the conversation goes sour or you both run out of things to say, would you rather questions help to keep such ill-fated conversations going. General questions could be fun to answer when dealing with a difficult date or group of people. For example

● “Would you rather live without the internet or live without cable TV?”
● “Would you rather be a great director or a very famous actor?”

See? No theme, just thoughts. Asking questions like this is another way to see if your date values credit for work done or fame for work done. Random but interesting insights could come up from answering that one.

● “Would you rather hear everyone’s thoughts, or have everyone hear your thoughts?”

Questions that make you go “hmm” before answering are guaranteed to revive and resuscitate any failing conversation. It could also be a great segue to other discussion topics just so the conversation keeps moving in the right direction.


With your look done right and your conversation skills polished, keep in mind that you should always allow your date answer honestly and meaningfully to enable them to open up freely. You get to know them much better if they’re free with you.

Moreover, you do not necessarily have to ask all these questions, sometimes go in-depth into some answers they give, and interesting things might come up- taking the conversation further.

Also note that there is no right or wrong answer, but answering “both” or “none” is against the rules. The fun is in the choosing. So, would you rather create great conversations at {EVENT DETAILS} or remain a wallflower with little to say? Come meet people, mix, mingle, and play the would you rather game amongst other activities. Remember to keep the conversation going.


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