Flirty Questions to Ask Your Ex Boyfriend
Twenty questions for finding out where an ex actually stands, in the order you would ask them: how he is, what he misses, how he explains the breakup now, what would have to change, and what he wants this to be. Read his answers before sending the next one.
The questions
Open any question for the note
How are you, actually?
Why ask it
The word actually is doing real work, because the reflex answer between exes is fine. Whether he takes the opening or bats it away tells you how much of a conversation is on offer tonight.
What made you answer?
Why ask it
It surfaces his reason for being in the thread at all: curiosity, loneliness, unfinished business, or genuine interest. An answer like I was bored is not flattering, but it saves you two weeks of guessing.
What do you miss about us, if anything?
Why ask it
The if anything gives him room to be honest instead of kind, which is what makes the answer usable. Missing having someone around is a different answer from missing you, and the difference matters.
What do you think went wrong, now that you have had time?
Why ask it
You find out whether he has a version of events with himself in it. If the story is still entirely about what you did, nothing has moved, however warm the rest of the conversation feels.
What is one thing I got wrong that you never told me?
Why ask it
Asking for it directly is the only way most people will say it, and it signals you can hear an answer. Be ready for something that stings, because a softened reply means he does not trust the question.
What would you do differently if we started over?
Why ask it
Specific answers, phone use, how he handled his family, going quiet in arguments, mean he has actually thought about it. Try harder is not a plan and should not be read as one.
Do you still hear certain songs and think of me, or has that faded?
Why ask it
Flirty and easy to answer honestly, since admitting to a song is safer than admitting to a feeling. The or has faded half is what makes it a real question rather than a bid.
What is your life like now that I would not recognise?
Why ask it
It asks him to describe the present rather than reminisce, and the amount of change is the useful part. If nothing has changed at all, you are talking to the same relationship in a new month.
Are you seeing anyone, and would you tell me if you were?
Why ask it
Two questions in one on purpose: the second is the one that gets tested later. Ask it early, before you have said anything you would want back if the answer is yes.
Is there anything you wanted to say back then and did not?
Why ask it
Breakups leave people with speeches they never delivered. This gives him permission to deliver his, and what he chose to swallow at the time is often the clearest picture of the relationship.
What made you happiest when we were together?
Why ask it
Warm and specific, and the answers are usually small: a routine, a drive, a particular morning. If everything he names is from the first few months, that is information too.
What did you learn about yourself after we broke up?
Why ask it
The honest version of this involves something uncomfortable. An answer entirely about how much he learned to appreciate you is flattery, not growth, and it predicts the same pattern returning.
Do you think we would be different people in a relationship now?
Why ask it
It asks about change without asking for a commitment, so it is easy to answer truthfully. Watch whether he describes changes in himself or only changes in circumstances.
What would have to change for you to want to try again?
Why ask it
This is the question that separates nostalgia from intent. A list you could act on means he has considered it seriously, and a shrug means the answer is no however affectionate the tone.
If I said I still had feelings, what would you say back?
Why ask it
Framed as a hypothetical so you can float it without handing over everything at once, though he will hear it as a statement. His hesitation, not his sentence, is the reliable signal here.
What do you want this to be: friends, something more, or nothing?
Why ask it
Naming all three options makes it easier to answer honestly than an open question does. Anyone who picks all of them at once is asking for access without a decision.
What are you not saying right now?
Why ask it
Best used once you can feel something being held back. It works because it is an invitation rather than an accusation, and the answer often reframes the whole conversation.
If nothing came of this, would you regret having had this conversation?
Why ask it
It lets you both acknowledge the risk out loud, and it tends to produce the most sincere sentence of the exchange. A no here is worth taking seriously rather than arguing with.
What do you want from me at this point?
Why ask it
Blunt, and much fairer than letting the ambiguity run. Vague answers about seeing where it goes usually mean he wants the option without the obligation.
Where do we leave it tonight?
Why ask it
A closing question that forces one clear outcome, so the thread ends on a decision instead of trailing off. Whatever you agree, hold it for a few days and see if he does.
Before you send the first message
Practical guidance for the conversation itself
Doing this deliberately
Decide what you want before you ask what he wants
Write down, for yourself, whether you want him back, want closure, or want to be wanted tonight. Going in undecided means you will take whatever he offers, and that is how people end up in an arrangement neither of them chose.
Ask one question and wait
Three sent in a row reads as an interrogation or as need, and it lets him answer only the easiest one. Send one, let him answer fully, then follow the part of the answer that surprised you.
Check whether he is single before you flirt
It is the ninth question here for a reason: ask it before anything you would regret if the answer is yes. If he is with someone, the flirtatious half of this list should stay unsent.
Read the answers for evidence, not for hope
The useful signals are specifics and follow-through: named changes, kept plans, direct sentences. Warmth costs nothing and is not the same as intent.
What the answers usually mean
- I miss having someone around is about the gap you left, not about you.
- Detailed regret with a named behaviour is the strongest sign that anything has actually changed.
- Fast affectionate replies late at night and silence during the day is a pattern, not a coincidence.
- If he asks you nothing back across the whole conversation, he is enjoying the attention rather than considering the question.
- Someone who wants to try again will usually propose something concrete, a call or a meeting, without being asked twice.
Common pitfalls
Reopening the argument that ended it
Litigating the breakup line by line turns a conversation into a rematch. Ask what he would do differently, then let the rest go, or accept that this is the fight and not a reconciliation.
Sending these while drinking
Late-night courage produces messages you cannot take back and answers you cannot trust. Anything you would only send at midnight is worth rereading at nine in the morning first.
Treating friends with benefits as a step toward getting back together
It usually settles into its own arrangement instead of moving on. If that is genuinely what you want, say so plainly; if it is not, do not use it as a route to something else.
Ignoring a soft no
Deflection, jokes and delayed replies to the direct questions are answers. Asking the same thing in a new way a week later rarely changes the outcome and costs you the friendship option.