Truth or Dare Questions for Your Ex Boyfriend

• What is the most embarrassing thing your ex boyfriend has ever done?

– Share a funny or cringe-worthy story about that one time when your ex-boyfriend accidentally tripped and fell in front of everyone at a party, leaving him red-faced and you struggling to hold back laughter.

• Have you ever cheated on me during our relationship?

– Get down to the nitty-gritty by asking if he had any sneaky rendezvous with someone else while you two were still an item. Prepare for some potential discomfort!

• Who was your celebrity crush while we were together?

– Unveil his secret obsession with a certain Hollywood starlet who may have made him weak in the knees, making you wonder how much competition this imaginary rival actually posed.

• Would you consider getting back together with me if given the chance?

– Delicately inquire whether there’s even a glimmer of hope left for rekindling what once burned so brightly between you both, hoping against all odds that maybe, just maybe, it’s not entirely over yet.

• Have you stalked my social media profiles since we broke up?

– Dive into the depths of digital curiosity and find out if he’s been silently lurking through your posts like Sherlock Holmes trying to crack a case. Perhaps he still can’t resist checking up on your fabulous life without him!

• Did you ever lie to me about anything when we were dating?

– Probe into those little white lies that might’ve slipped from his lips during your romantic escapades together. Remembering them now might make them seem more amusing than hurtful.

• What is something that annoyed you about me when we were a couple?

– Give him an opportunity to vent (in good humor) about those quirky habits or idiosyncrasies that used to drive him slightly bonkers but somehow managed to keep things interesting between you two.


• Call one of your friends and tell them how much you miss being in a relationship with them.

– Challenge him to make an awkward phone call where he confesses his longing for the good ol’ days, leaving both parties feeling bewildered and amused.

• Send a text to your ex’s best friend saying that you still have feelings for them.

– Push him out of his comfort zone by daring him to put his heart on the line (albeit as a joke) and watch the chaos unfold between friends who may or may not be willing participants in this humorous charade.

• Post an embarrassing photo of yourself on social media with the caption “Missing my ex like crazy!”

– Encourage some self-deprecating humor by urging your ex-boyfriend to share a hilariously unflattering picture accompanied by an intentionally melodramatic caption. It’ll surely raise eyebrows among mutual friends!


• Do you regret breaking up with me? Why or why not?

– Get ready for some soul-searching honesty as he reflects upon whether parting ways was truly worth it or if there remains even a smidgeon of remorse lingering deep within his heart.

• Did you ever badmouth me to your friends after we broke up?

– Dive into potential post-breakup gossip territory, questioning if any juicy tidbits about your personal life slipped from his lips during those late-night bro sessions. Prepare yourself for possible revelations!

• Have you been dating someone else since our breakup?

– Curiosity strikes again! Find out if Cupid has struck another target since things ended between you two, potentially opening doors either towards closure or reigniting old flames.


• Call your mom and tell her that you want to get back together with your ex.

– Oh boy, time for some family drama! Dare him to take that leap and face the music while explaining why rekindling love is suddenly at the forefront of his mind. Brace yourself for parental reactions!


• Did any of our arguments contribute to our breakup, or was it something else entirely?

– Uncover the root cause behind your relationship’s demise by asking if those heated debates played a significant role or if there were other factors at play. It might provide some valuable insights.

• Do you think there’s a chance for us to reconcile in the future?

– Lay all cards on the table and ask him about his hopes for a potential reconciliation down the road. Prepare yourself for an answer that could either shatter your dreams or reignite hope within your heart.

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