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"Mid-life Crisis" Car Purchase

I wouldn't say that I am actually having a mid-life crisis. I turned 50 in January and as some of you may already know from a couple of my other threads I'm about to be single again. I have been wanting a new car for a while now and since I will have no one else to please but myself I'm thinking about getting something more fun and interesting. With the exception of a '69 Dodge Charger that my parents bought me in the mid 80's, I have had nothing but inexpensive and practical cars my whole life. My current car is a 2007 Chrysler PT Cruiser. I got it because it was cheap and had plenty of room in the back to haul gear. Prior to that I had a Hyundai Elantra and before that a Dodge Caravan. Yawn!
Now I'm looking at modern muscle cars and since I'm a Mopar guy I'm leaning toward either a newer Challenger or Charger. The Charger is a bit more practical since it is a four door sedan but I really like the look of the Challenger. I'm going to check out the Camaro and Mustang as well. Whatever I get it will be used, probably in the range between 2012-2015 and I would like to stay in the low $20K range as my max price.
Curious who else has made a less practical car purchase and did you later regret it?
What are some other models I may want to check out?
 
I don't think I can classify my red 2015 Toyota Tundra as a true, "mid-life crisis" vehicle because I've wanted to own my own full size truck for a long time.
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life is short..........go fast

I'm shopping for a Challenger R/T at the moment, I'm not sure I could afford the insurance on a SRT. I like the fact they resurrected the 392 though, 475 hp. yeah baby.

Yeah I haven't even thought about what the insurance rates will be like on some of these cars I'm thinking about! The R/T is about as much money as I want to spend anyway. Hopefully the insurance won't be terrible.
 
Other that my free Subaru Forester, none of my cars/trucks are practical. I've driven mid-life crisis cars since I was 18 and I recently turned 49.

I've got three lifted trucks, A street legal 10 second Camaro (that I've owned for 31 years), a 12 second Z/28 and a 68 Elcamino SS396.

I refuse to grow up.
 
I'm a recent convert to being a Mopar fan.

After 30 years of driving Ford F250s, I''m now driving an AWD 2015 Dodge Charger, and dang, it is awesome. Fun Fun Fun... It scoots.

Maybe I'm having my midlife crisis at 57.

My wife drives a 2014 Durango and it's the only thing we currently own that my upright will fit in to, so we'll keep it, I suppose.

My 18yo son drives a 2014 Chrysler 200 and loves it.