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Is there a word for when someone (often a middle-aged father) constantly tries too hard to keep up with 'trends'?

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Ummm... I suppose wannabe trendy wouldn't do, since a wannabe normally has overtones of misplaced youthful optimism rather than regression to a second childhood. –  FumbleFingers Apr 15 '11 at 19:44
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"Let me explain something to you. Um, I am not 'Mr. Lebowski'. You're Mr. Lebowski. I'm the Dude. So that's what you call me. You know, that or, uh, His Dudeness, or uh, Duder, or El Duderino if you're not into the whole brevity thing." –  Robusto Apr 15 '11 at 19:46
    
@Fumble: Well, I stole "wannabe" and added to my answer anyway. Hope you don't mind. :P –  MrHen Apr 15 '11 at 19:49
    
"Wannabe" could refer to anybody who aspires to something they are too lazy/untalented to achieve, though. –  lotsoffreetime Apr 15 '11 at 20:02
    
Anyway, I have teenage children myself, and I admit I make a bit of an effort in that direction. Out of paternal interest cum sociability, I like to think, rather than just playing out some neurotic fantasy. Perhaps I should ask them if they have a word for it - and if so, is it complimentary or pejorative? –  FumbleFingers Apr 15 '11 at 21:12
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4 Answers

An Ed Hardy customer. :)

In all seriousness though, I like 'painfully hip' for this one. As in 'The painfully hip dad couldn't resist wearing his Ed Hardy shirt to the PTA meeting'. Also, along those same lines, you can say 'tragically hip.'

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Other than taking any typical adjective for trendy and negating it (uncool, unhip, untrendy) you can try one of the following:

  • desperate
  • square
  • old-fashioned
  • behind the times
  • antique / antiquated
  • ancient
  • dated
  • wannabe
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Now I come to think of it, all your 'synonyms' are uncomplimentary. So perhaps you should add cool, which has been around for decades in this sense. "Yeah guys, we can smoke a joint at my house. My Dad's cool". –  FumbleFingers Apr 15 '11 at 21:16
    
@Fumble: I was under the impression that this is exactly what was requested? –  MrHen Apr 15 '11 at 22:15
    
cover all bases, MrHen! –  FumbleFingers Apr 16 '11 at 3:50
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There may not be a specific word for the thing you describe, but these might do for you.

The term "mutton dressed as lamb" fits, though this isn't a single word as requested (note that "dressed" refers to food dressing, not clothing) and is usually feminine-specific.

"Middle-aged hipster" fits too, but again is a little specific to the type of thing it describes.

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I like poser

From the Dictionary of American Slang and Colloquial Expressions:

Someone who pretends to belong to a group only by affecting the attributes of the group. (See also mod poser.) : What's he doing here? He's just a poser, looking for dates.

However, it doesn't specify the age of the person.

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It's not actually a slang term - it's a corruption of the French poseur. –  MT_Head May 26 '11 at 6:08
    
I'm going to stick to my guns on this one, French corruption or not. I found an entry that backs my thinking (see above). It exists as a standard term, but in the way that I'm using it is slang or informal. –  gbutters May 26 '11 at 10:46
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