If you’ve just been fighting or he’s angry, now might not be a good time to poke and prod him. Listen to what he’s saying. If he’s confiding in you that he’s heartbroken over his dog’s death, he probably needs a hug more than he needs tickle torture. Wait until you’re somewhere relatively private and have room to wrestle a little and not injure yourselves. Make sure he’s not holding a hot beverage or something that might injure him or you when you catch him by surprise. Don’t try to tickle him when he’s playing video games or absorbed in something that is really important to him (even if you are annoyed that he’s not paying attention to you). This is when tickling is just annoying, not fun. If you two are joking around and he’s in a good mood, he probably won’t mind a little tickle.

Poke him in his side, just above his hip or in his ribs and see if he giggles. Give him a hug and “accidentally” tickle his armpit. This is one of the more ticklish spots on most people. If he’s laying down with his shoes off, gently run your toes along the bottom of his feet and notice his reaction. Kiss him gently on the neck and exhale through your nose so the air hits his ear. See if he gets goosebumps on his neck.

The key is to use a fairly light touch–if you use too much pressure tickling can quickly become unpleasant and even painful. [2] X Research source Try and get him to stretch his arms above his head so he is fully exposed for an attack. Stretch first and he may instinctively copy you. Or say something like, “who wants ice cream?!” and raise your hand. He’ll probably do the same (unless he hates ice cream). If he’s laying down you can straddle him so he can’t escape and he’s more vulnerable.

Be careful that you don’t get kicked. He may begin to jerk his legs away from you and kick you in his struggle to escape.

Don’t tickle him for more than 15-20 seconds. If he says he’s laughing so hard he’s going to pee in his pants, believe him and stop tickling.

Tickling can be a very flirtatious action, and it’s likely that, during or after the struggle, someone will initiate making out or fooling around.