How does one be less serious and have more fun?

So, ask yourself what you would do and how would you live if you won the lottery and had no money worries. That may be a good jumping-off point. Maybe riding the motorcycle around the county on weekends might be a good compromise - maybe w. someone you care about sitting behind and hugging you

I agree with answer one, but I have this to add: My dad tought me not to worry about things I cannot change, like things in the past. Dwelling on things you can no longer change keeps you from concentrating on making things better in the future.

My sister once told me to live in the moment. When it comes to de-stressing I think there is little other advice that can do as much for you. try to focus in on the immediate around you.. you're sitting at a computer right now, for instance. try to notice something odd about your surroundings that you never noticed before. find humor in it. this is a start.

second.. segregate work from play. come home and do something you've never done before. it doesn't have to be a crazy life changing experience, to start. just something new. I always say that I'm a fan of 1sts. try to have at least one 1st a day. if you have the money: go jet-skiing. play tennis, and don't worry about whether or not you suck. play a video game; sit on a row boat with a beer and read a book in the sun; lay in a hammock and swing more than you would otherwise; go to a public library and find the fiction section - pick something with the craziest title; sit at a cafe and watch people while text-messaging people in your phone who you haven't talked to in ages.. just say "hi" with a smiley face.... :)

I'm rambling.. but the point is: you don't have to be extreme to try new things. enjoy yourself!! :-) best o' luck!

sorry to double-post.. i just wanted to emphasize that you really should go jet-skiing. :)

this might sound odd, but do something that scares you. If you take risks, you'll have more fun. Do something out of character that you've never done before--and if you're overly contemplative, try something physical and active--take a dance class, yoga, etc. Buy a bicycle and ride it around--I have found that it's hard to feel too serious when you're on a bike with the wind in your hair. Join a team or a club--local softball league, kickball league, ultimate frisbee. I think that approximately 82% of fun occurs outside, so making sure to spend more time in the sun this summer will raise your fun quotient. If you are wearing sunscreen, it must be fun, right?

while this is a distinct question, some of these ideas may apply: http://www.fluther.com/disc/988/how-to-get-out-of-a-funk/

Quitting to ride a motorcycle around the country's not the answer? Then why did you bring it up?
You're an executive?
Then make something happen.

As my roommate likes to say, "Maybe partying will help."

I left work early today and took my girls to the pool. Sometimes I forget to have fun but crazy 8 and 11 year old kids will can snap you back to what's important.

that's a really interesting question. you don't just want to change your activities, you want to change your approach to life, your motivations and instinctive/habitual responses. and that, after many years of building the style that is now your way of moving through the world. i think this will be a tremendous experience (and challenge) and i hope you report back how it goes. i'm curious to hear what's you do.

i wonder if something like improvisation classes might help inspire some playfulness--it's a playful context and meant to get you having fun with others.

i'm also a big fan of role modeling. i might try to spend gobs of time with folks who really savor and enjoy life. pick some people and stick to them. try to be around fun people as much as you can be. i'm not sure if this kind of transformation can come from within as easily as it can come from role modeling other people who do it well.

Perhaps write a realistic wish list of what you would like to accomplish in life (fun related or dreams) and try to find the time for it. Its nice to have a goal in life.

One of the lists I have is tandem skydiving over Monterey Bay, California with two of my college friends when we turn 40 in a few years, go visit Italy and experience the gondola and countryside with my hubby, and to visit Greece. Also parasailing is another wish. It can be small, big things come in small packages like volunteering. etc.

Hope this helps. Have fun making a wish list if you are interested in doing that. I started to make this wish list after I read a story how a person lived life to the fullest at a funeral and not to be sad. Should celebate how he lived his life and that some or all of his dreams came true. Someone enlarged his wish list and he or she accomplished things in life. Like drinking coffee with the view of Eiffel Tower in Paris, sunset on an island or something. That inspired me to continue to live life to the fullest and make a fun wish list.