Funny Questions to Ask Your Ex
Twenty lighthearted questions for an ex you are genuinely on good terms with: the habit you used to tease them about, the argument that made no sense in hindsight, and the stories your old friends still bring up. Check the room first, and drop any question they sidestep.
The questions
Open any question for the note
Do you still have that habit I used to tease you about?
Why ask it
A safe opener because it is affectionate rather than pointed, and it signals early that you are here to laugh rather than to relitigate anything.
Do you still eat that food combination I never understood?
Why ask it
Food quirks are the least loaded shared memory available. If this gets a short answer rather than a defense of the combination, they may not want the nostalgia at all.
What's the funniest song that takes you straight back to that era?
Why ask it
Music dates a period without anyone having to characterize it, which makes it a much easier route into the past than asking about the relationship itself.
What's the most ridiculous thing we ever argued about?
Why ask it
Note the word ridiculous. It points them at the parking-space argument rather than the real one, and if they reach for the real one anyway, this conversation is not ready for that.
Which of our inside jokes would make no sense to anyone else?
Why ask it
Acknowledges shared history without asking either of you to evaluate it. Usually both of you remember the joke and neither remembers where it came from.
What's the most ridiculous thing we ever waited in line for?
Why ask it
Shared misadventures point the joke outward at the situation instead of at either of you, which is the safest kind of story you have together.
Which of my terrible film picks do you secretly still defend?
Why ask it
Letting them tease your taste rather than the reverse is what makes this land. Volunteering yourself as the target is how these conversations stay friendly.
Do you still make that face when you're confused?
Why ask it
Small physical habits are noticed only by people who lived with you, so the answer is a reminder of familiarity rather than intimacy. Keep the tone light or it reads differently.
Do you still keep that collection I never understood?
Why ask it
Harmless and specific. Whether the collection grew, stopped or got thrown out is a quick summary of what happened to them since, without you having to ask.
What restaurant or place did we accidentally ruin for each other?
Why ask it
Most former couples have one venue neither of them goes to any more. Naming it is funny, and it often turns out only one of you was avoiding the place.
What's a skill you only have because of me?
Why ask it
A generous question that lets them credit you with something without either of you getting sentimental. Expect something small: a recipe, a route, a card game.
What did you inherit from my taste in music that you'd never admit?
Why ask it
The phrase never admit is doing the work here, because it turns a compliment into a confession and keeps the register comic.
What's the strangest thing that has reminded you of me since?
Why ask it
This one can go either way, so watch the answer. Something absurd means the mood is right, and anything wistful means you should steer back to safer ground.
Do you still hold that superstition I could never talk you out of?
Why ask it
Beliefs people keep despite being teased about them are usually inherited from family, so this often ends up being a story about their grandmother rather than about you.
What's the funniest way someone has described the two of us?
Why ask it
Puts a third party in the frame, which takes the pressure off both of you and usually produces something flattering neither of you had heard.
What's something ridiculous you've done lately that I'd have made fun of?
Why ask it
Present tense, which keeps this from turning into an inventory of the past. It also quietly acknowledges that you no longer get a vote on their choices.
Do you still have that photo of me you used to threaten me with?
Why ask it
Works only if the photo was always a running joke. If it was ever used as real leverage, skip this and do not bring it up.
What's the funniest thing our old friends still bring up about us?
Why ask it
Friends usually keep the flattering stories, so this tends to produce something warm. It also tells you what the two of you looked like from outside.
What's the funniest thing you've told a new friend about your ex?
Why ask it
Only ask this if you are ready to be the punchline, and only if the answer being nothing would not sting. If either is untrue for you, leave it out.
What's something from back then you can only laugh at now?
Why ask it
A good closing question because it invites perspective rather than a verdict. If the answer is nothing yet, that is honest and worth accepting without pushing.
Keeping this friendly
Practical guidance for the conversation itself
Before you ask anything
Only if the friendship already exists
These questions work between people who already text about ordinary things. If your last few exchanges were logistics about a lease or a pet, nostalgia will read as an opening move rather than a joke.
Consider who else is affected
If either of you is with someone new, reminiscing about shared habits and inside jokes is the kind of conversation that is much easier to explain if you would be comfortable having it in front of them.
Pick a setting with an exit
Coffee, a walk or a group setting all give either of you an easy way to end it. A long dinner or a late-night call raises the stakes on every one of these questions.
Signs to stop or change direction
- Answers get shorter with each question rather than longer.
- They redirect to the present, to work or to mutual friends more than once.
- A light question about an old argument gets a serious answer.
- They laugh but do not ask anything back.
- You notice you are the only one supplying memories.
What these questions are not for
Reopening the breakup
Nothing here asks why it ended or whether they regret it. If that is the actual question you want to ask, do it plainly and separately rather than smuggling it in behind a joke about their taste in films.
Fishing for information about someone new
Questions about their current life are fine as long as you would be satisfied with a vague answer. If you are hoping for a specific one, you are not really joking.
Teasing that only goes one direction
Old habits and quirks are affectionate when both of you are being teased. A run of questions aimed only at them turns into a list of complaints you never got to deliver.