Truth Or Dare Questions For Your Boyfriend

Truth or dare is classic fun for many people, young and young at heart, but it can also serve as a method for a new couple to get to know each other or those dating for a while to bond further.

Go to for guidance on getting the truth from a mate.

The idea is to set the rules upfront, so everyone is on the same page. No one wants to be caught off guard by an uncomfortable question.

If you decide to play a fun round, you can play the nice version, or you can venture into darker territory with an in-depth variation to try to get some details the guy has been holding out on. The problem is that you’ll need a worthwhile dare to suffice when your significant other chooses to pass on the answer.

Some couples play by text to make it more casual and comfortable for the other person. That takes away from seeing the expressions as the questions are asked, plus how do you know whether they complete the dare?

Let’s look at a few truth-or-dare questions you can ask your boyfriend on date night. You’re encouraged to play face-to-face instead of via text. Let’s get some ideas.

Truth Or Dare Questions To Ask Your Boyfriend

Sometimes it can be tricky to get a guy to communicate openly. Vulnerability is not a strong suit, especially in the beginning. What could help is playing a game where they don’t realize they’re essentially having a conversation like with truth or dare.

There are different renditions depending on the sort of relationship you have. Perhaps you’re still relatively new and getting to know each other. You would stick with the friendly version, just generic albeit fun questions.

Girls settled into a longer-term couplehood might have heavier questions making their boyfriends uneasy for a little darker game, leading guys to a range of dares to spare their answers.

However you choose to play, ensure everyone knows how the game will go upfront, so no one is caught off guard. Let’s look at some of the questions many ladies ask their significant others.

  1. What would you consider your guilty pleasure

Everyone has something they like to indulge in without revealing to anyone, including you, the secret pleasure. The benefit of opening up about what your guy enjoys is that you could help him realize more of his fantasies if he were to let you know what he desires.

Answering a question like this can put him in a vulnerable place. You should offer some details of your own to put him in a more comfortable position to share then how he feels.

  1. What about women would be a turn-off

It’s easy for a man to share the things that he likes. But sometimes, it can feel as though he’s saying only what you want to hear. Boyfriends like to offer compliments to make their girlfriends feel good but grow leery when it comes to letting them know what not to do.

He won’t be as willing to tell you things that you do that bother him but if you ask about other women, he’ll likely be vocal about the things that drive him crazy about the opposite sex.

  1. What is the most foolish thing you’ve done in public

The idea with a question like this is to help your boyfriend realize it’s okay to be embarrassed around you because you won’t criticize or judge his behavior. You’ll laugh with him, but the secret will be safe with you from then on.

It helps you establish a deep connection, and he can feel a stronger sense of trust with you mainly because you don’t tease or tell.

  1. Do you have any regrets, and which is your most significant to this point

No one wants to reveal regrets making this a tricky question that could lead to a dare, but you can get an answer with sufficient coaxing. Everyone has regrets, but these form the person you eventually become.

If your boyfriend can share a past regret, it will help you better understand who he is and why he handles the relationship the way he does. If he chooses the dare, save this question for the next time because it’s ideal for the game and the partnership.

  1. What is the weirdest thing that’s ever happened to you

Guys love to share stories with anyone who will listen. If you open up the gate, your boyfriend will excitedly share a story of odd and strange events that have occurred over the years in his life, not just one event that he deems to be the weirdest, but all the off-the-charts happenings.

This truth or dare question will take up a significant portion of the game because the two of you will be comparing notes and branch off into an evening of conversation, forgetting about the game, a bonding moment. That’s a definite good thing.

  1. Who do you envy most

Again, another vulnerable moment is having to admit there’s someone that he feels is superior in some way to himself, but it’s good to talk about the person your boyfriend carries envy for. This gives you the opportunity to point out his personal strengths that perhaps this other person doesn’t share.

Let him know there will always be people we admire for their unique qualities, but it’s essential to recognize that these attributes merely make everyone different, not better. The person your boyfriend envies might very well be impressed with the talent he demonstrates.

Final Thought

These are a mere sampling of what could be many more thought-provoking questions you can ask with a good game of truth or dare. You can keep it light and funny or go deep and insightful; just make sure however you want to play the game, your boyfriend is on board, or you might be doling out loads of dares. Go here for details on flirty dares you can use with your game.