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A funny night starts with a topic, not a joke: a ridiculous hypothetical, a weird opinion, a story you both still retell. Pick one, say it out loud, and let your partner take it somewhere unexpected.
Try this one right now: “If you had to describe our relationship as a type of weather, what would it be today?” Argue about the answer. The rest of this page is a menu of what to talk about next, and the full questions to ask your boyfriend collection is there when you want more.
Every question here comes from Lolo Cards - 5,200+ conversation cards for iPhone.
Why do funny topics work better than funny questions?
A question can feel like an interview. A topic feels like a game you both get to play. “Okay, rank the worst ways to be woken up” gives your partner a job: to be funny alongside you.
In a review of 39 studies with more than 15,000 participants, University of Kansas researcher Jeffrey Hall found that being seen as funny is not strongly tied to relationship satisfaction. The humor a couple creates together is. In his words, “It’s good to have humor. It’s better to see it in your partner. And it’s best to share it.” That is correlation, not a promise, but it suggests you can skip the stand-up routine and build one together.
So aim for topics where both of you can add a line.
What are the best ridiculous what-ifs?
What-ifs are the easiest way in. Nobody can be wrong, and the debate is the point. Start with these:
- If you had to be an emoji forever, which one would you choose?
- If you had to name your phone, what would you call it?
- If you had to be famous for one weird thing, what would you want it to be?
- Who’s most likely to survive a zombie apocalypse?
The zombie one gets competitive. You will both rank yourselves higher than the other person and then defend it with evidence. Keep score. Say “you’d last four minutes” with a straight face.
Then make up your own. Which of you would be worse at a heist? What would your two-person reality show be called? Who gets voted off first in a cooking contest? Your partner’s face while they think about it is half the fun.
How do you find the weird opinions?
Everyone has a few opinions they have never defended in public. Is a hot dog a sandwich? Is cereal soup? These are low stakes on purpose. You get to see how your partner argues when it doesn’t matter, and it usually turns out they care a lot.
House rule: take the other side on purpose. If your partner says pineapple on pizza is fine, you are suddenly its biggest enemy. Play it for two minutes, then switch.
These questions pull out the odd stuff:
- What’s the weirdest thing that we both love?
- What’s your favorite weird habit of mine?
- What’s a weird talent you wish you had?
- What’s the most ridiculous thing you’ve ever said with total confidence that turned out to be wrong?
Which running jokes are worth bringing back?
Every couple has a few: a word only you two use, a story that gets worse with each telling, a nickname that started as a mistake. They usually hide in plain sight, so go looking.
Researchers at Appalachian State University studied something close to this. They interviewed 52 couples and asked each to recall a different kind of memory. Only the couples who recalled a time they laughed together reported an immediate rise in relationship satisfaction. Recalling laughter alone, or a happy moment without laughter, did not produce the same result. The lead researcher said nobody knows how long the effect lasts, so treat it as a nice side effect, not a fix.
The practical version is simple: dig up the old laughs. Ask:
- What’s the first time you remember laughing with me until it hurt?
- If you could live in any decade, past or future, which one would you choose?
Try the old trick of retelling a story from the other person’s point of view. It gets worse and funnier every time.
What if the jokes fall flat?
Then you laugh at that, too. A flat joke is just another running joke waiting to happen.
A few things help:
- Ask a follow-up before you add your own. “Wait, why?” is the funniest question there is.
- Keep teasing about the situation, not about your partner. Hall’s review warns that aggressive humor inside a relationship is a bad sign, so the target is the zombie plan, not the person.
- If one of you is tired or stressed, go gentler. A soft one like “What’s the weirdest food combination you secretly love?” works when you have no energy for a bit.
- Phones face down. Funny dies when someone is half-scrolling.
If you want more of the same mood, the funny questions collection is full of them, and the bored on the couch guide takes you from silly to real when you’re ready.
End with a question that works as a laugh and a hint: “What’s a weird talent you wish you had?”
