How to Joke with a Guy

Getting Comfortable Around Him

Ask him a few basic questions. Once you’re comfortable saying hello to him, start a conversation by asking some basic questions. You don’t need to interrogate him or ask him anything personal. Something casual like “How’d you do on that math test?” or “Are you going to the game this weekend?” can get the conversation going and help you feel comfortable. Pick a time when he's just hanging out casually. If you ask him questions when he's trying to get to his next class or while he's waiting to find out if he made the team, he'll get frustrated.

Keep your conversation casual. If you want to have a fun, joking relationship with a guy, it’s important to keep the conversation light and casual. Don’t ask personal questions right away, and don’t try to talk about his problems all the time. Subjects like the weather, sports, or people you both know are great casual conversations. You can also try talking about mutual friends, common classes, or a band shirt or jersey he's wearing. If he does start to talk about his personal life with you, be supportive and honest with him. You can still joke with him later! You can talk about your own problems or give advice, but make sure you listen to him first.

Watch how he talks to his friends. Finding out how he interacts with his friends is a great way to learn what kind of humor he likes. If he spends a lot of time laughing and jumping around, he’ll probably appreciate wacky jokes or physical comedy. If he’s usually quiet and serious, he might like dry humor.

Listen to the jokes he laughs at. An even better way to get insight into his sense of humor is to see how he reacts to other people’s jokes. Does he do a fake laugh and then change the subject when someone makes a pun? He probably doesn’t like those. If he laughs so hard he starts coughing when he hears a knock-knock joke, he’ll probably love to hear yours. Joking around is a two-way street, so it's important to listen to the other person's comments and respond in kind. Pay attention to their tone and body language, and use that as a guide for how to respond and to joke.

Find out if any subject is off-limits to him. Everybody has certain things that they won’t joke about. If you want to avoid insulting him or hurting his feelings, find out what his taboo topics are. You don’t have to actually ask him--this is information you learn gradually. For example, if his mother has passed away, your-mama jokes are probably a bad idea. If he feels bad about his weight, don’t make fat jokes. A good way to figure out which subjects are off-limits is to watch his reaction when people make extreme or offensive jokes. If he cringes or flinches when someone jokes about death, he probably doesn't think it's funny.

React appropriately if a joke backfires. If you tell him a joke that offends him or hurts his feelings, the right thing to do is to apologize and promise not to joke about it again, even if you don't think it was a big deal. If you told a joke that just wasn't funny, start making fun of the joke yourself!

Laugh if he tells you a joke. If he tells you a joke first, laugh! This lets him know that you like to joke around and you have a sense of humor. If you didn't find his joke very funny, you should at least smile a little to show that you understand it was a joke. You do not have to laugh at cruel or offensive jokes! Simply tell him that it wasn't funny.

Telling a Joke

Use observational humor to show that you're a quick thinker. Observational humor is making a joke about something going on around you. They’re usually about how ridiculous the situation is. It’s hard to come up with observational jokes in advance, but if you see something funny happening around you, go for the joke! For example, if your teacher keeps changing the due date of your final paper, you could turn to him and say “This is so crazy! I’m going to have grandkids in high school before she picks a due date.”

Show how approachable you are by making a joke about yourself. Many guys like hanging out with people who have a sense of humor about themselves. Try making a joke about one of your characteristics. It’s a great way to show that you’re down to earth and approachable. If you're hoping this guy likes you, he might tell you something good about yourself in response. Don’t say anything really negative or mean about yourself--it will make people uncomfortable. Keep it lighthearted. For example, if you have really long hair, you could say “My hair is so ridiculous. I could weave a blanket out of it and give it to your for your birthday.” Or if you hate waiting, you could say “I’m so impatient! It’s like I’m secretly a two-year-old in disguise.”

Show off your silly side by telling a corny joke. Puns and “dad” jokes are popular with a lot of people because they’re so bad and corny. If you aren’t good at coming up with jokes, try telling one that you already know is bad. It takes a lot of the pressure off! Just keep smiling during the joke so he knows you know it’s a bad joke. For example, if he says “I’m hungry,” you can respond with “Hi Hungry, I’m Taylor!”

Be witty by making a dry joke. Some guys appreciate dry, deadpan jokes about serious topics like life, death, and art. These jokes are always delivered with very little expression and no laughter. These kinds of jokes can take a lot of practice to get right. A basic example of a dry joke is to make a reference to a historical event like an assassination or a battle, and then to ask “Too soon?” in a very serious tone.

Send him a meme when you're online. This is a great way to joke via text or social media. Just pick out a meme you think is funny, and send it to him! Try to send a meme that’s currently popular and that you know he likes. Meta-memes are a great way to get a laugh. In these memes, you’re making fun of the actual meme itself--its format, its content, and why people think it's funny. These are especially good if the meme has gotten really popular and you’re worried he might not be into it.

Do an impression to show him you're outgoing. If you’re good at imitating other people, try your skills out on him! You can do imitations of famous people or people you both know. To do a great imitation, it helps to focus on how the person says things, rather than their exact tone of voice. For example, if you have a high-pitched voice and you want to imitate your deep-voiced science teacher, focus on what he says and the speed he says it at. Don’t do cruel imitations of people you know. That can make things difficult for you, especially if your guy friend actually likes the person.

Tell a knock-knock joke. Knock-knock jokes are classics for a reason. Everyone likes hearing them and laughing about how silly they are. There are knock-knock jokes about every topic imaginable, so you don’t even have to think of one--just search online to find the perfect one for your guy. If your guy friend likes meta-humor (humor that is unusual and self-referential), try searching for a knock-knock joke about knock-knock jokes.

Make a positive joke about him to show him you like him. Joking about someone else can be a little risky, but if he seems to have a sense of humor about himself you can make a mild joke about him. Remember to make your joke about something that’s considered a positive characteristic. For example, jokes about him being bad at sports or nearsighted might not be a good idea, but jokes about how tall he is or how good he is at chemistry might make him smile. Try something like “I saw you in the school play, you were great! When you win an Oscar, are you going to pay for the limo and my dress, or should I start saving up?” If you have a flirtatious, romantic thing going on, you can make jokes about how great you are together or how much you love him.