When life is bleak, we're not going to laugh no matter what. To see the humorous side of things, we have to be willing. So work on helping him be happy (making someone happy is impossible -- they have to want it) by being your awesome self and gracing his presence with it. By being positive and fun, you're really doing all you can. Be his friend (or whatever is fitting for your relationship), do little things for him, and just try to make his life easier (especially if he's been dealt a sour deck of cards). Let him see the bright side of life so the humor can start flowing. There are few things funnier (and mood-uplifting) than a person that can embarrass themselves and just roll with it. There are few things worse than a person that embarrasses themselves and gets all self-conscious and shameful. So when you spill that soda on yourself, just say that you're saving it for later and that brown looks better on you than white, anyway. Also, it's like two-for-one perfume. You're just being frugal! Studies actually show that embarrassing yourself can actually get people to like you and trust you more. It sort of makes sense -- when you show you're down-to-earth, light-hearted, and just a plain human like they are, it takes away any possible intimidation and stress. Slapstick, physical comedy is the only kind of comedy that's been around for all of human history -- and it still is for a reason. If the witty asides don't come to you naturally, don't stress! You can convince him you're the funniest thing since Tina Fey by just using your non-verbal hilarity.  Popcorn? Uh, yes, please! It's time for a who's-got-better-aim contest. And spaghetti? It's totally Lady & the Tramp time. Standing in line for your favorite movie? Bored so incredibly that you're practically gnawing off your arm for something to do? Why would you not bust out the macarena? As long as he's the type that doesn't embarrass easily, that is.  Try play-fighting, tickling or play-attacking him. The bond of human touch is strong as steel. Is it time for a thumb war rematch yet? Laugh yourself.  You don't need a good reason! Laughing is a chain reaction that often causes other people to laugh. And it will make you happier, too! . If you're visibly high strung or stressed, no situation you're in will be happy-go-lucky and funny. You know that one person that's always a negative Nancy? Don't be the party pooper! Relax. It's the only way to be yourself, be silly, and create an environment where the laughter will naturally flow. If you're relaxed and enjoy each other's company, the laughter will spontaneously start itself! If he's not laughing at your jokes, it's fine. You think you're funny and that's all that matters. If he sees you in your element, being natural, there's nothing to not like. So take a breath -- you got this.
Help him be happy in general. Be willing to embarrass yourself. Get physical. Relax