Anyone in their fifties who wants to be 'cool' is doomed to failure just by reson of trying to dress mutton up as lamb. I'm going to be fifty soon and am thouroghly enjoying the transition to crusty old dinosaur - nobody at work, wheree they are all younger than me by decades in some cases - messes with me or expects me to do something I don't want to do. Acutally - I guess I am ABSOLUTELY SUPER COOL really because I don't give a damn what a bunch of kids think of me! : )

No. I think that the act of "trying to be cool" or changing who you are just so others approve of you is the most embarassing, cringeworthy thing one can do. Be yourself, know what you are good at and do not be phased by what young people think of you. As long as you play to your strengths you will automatically be "the bomb".

As far as I'm concerned (as a 23 year old), the people I most want to be around are confident within themselves. They are not trying to be "cool" or "the bomb" (whatever that's supposed to mean). The "coolest" 50s+ people I have known were like my former high school history teacher - who would introduce me to musicians I'd never heard of, and trade books with me. I was able to learn from him, but never felt like he was portraying a "You're ok, kid, but with my help you can be much improved" kind of attitude.

If you average, nice people in your 50s would like to be considered cool, you can do one of two things: stop trying, or buy kids like me - young, attractive minors - alcohol. Instant cool.

Whatever you do don't be yourself. People hate that. Especially cool, young amazing people such as myself.

As a nice person in her 50s, I'd say step one is not to ask this question. You may wish to keep informed about current events, celebs, music - but do it because it interests you.... Be who you are regardless. Ex.: I'm not big on tats but I don't judge a person just because of them.

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Pretend to be senile. It works, the "Youngins" will want to be around you because you'll be freaking hilarious.

Jazz, I'm only a few years behind you, and having just read all the answers that proceed mine, I have to agree with the majority here: you be you. I have never ever been part of the "in" crowd, which probably has a lot to do with my answer. I learned very early on in elementary school that whatever 'cool' was, I sure didn't have it. Of course, by about age 12, this bothered me, and I'm sure I did a lot of even nerdier (is that a word?) things to try and "be cool", which only buried me deeper in uncoolness (ANother non-word). So, by my late teens, I had been so well ingrained at being outside the in-circle that I stopped trying, and have never ventured near it again. After 4 decades on this big blue marble, I not only know I'm not cool, I hardly know what cool is, and what I do know of it, i want no parts of. My favorite music is from the 1980s, followed by the 1970s, then the 1960s. I still use 1970s slang (right on, dig, groovy, etc) and I don't care that I don't know the new slang. I don't follow fads. I haven't run out an gotten a tattoo or body piercing, nor do I plan to. No one in the next car can hear my radio or CD. I dress like a man in his 40s, not like a man in his 40s trying to look like a 20-year-old. I've never seen one episode of "Friends", "Sex & the City", "Dawson's Creek", "American Idol", "The Gibson Girls", "Desparate Housewives", any of the vampire movies/TV shows, just to name a few, and I don't think I'm missing anything. I do not have a blog. I am not on facebook, myspace, or any other such site. I do not even know what tweeter looks like. I just got a cell phone about 3 years ago, reluctantly. I've never bought anything online. There are no pictures of me circulating the internet, naked or otherwise, having sex or otherwise. I am as square as a math project, and, in the words from one of my favorite songs, "Lovin' Every Minute of It"!