The film follows the lives of a group of single guys who are aspiring entertainers seeking their break in Hollywood in the mid-90s. Mike, played by Jon Favreau, has not gotten over a breakup with his girlfriend from New York six months earlier. His friends Rob, played by Ron Livingston, and Trent, played by Vince Vaughn, do what they can to cheer him up and get him to move on. Mike is presented with ample opportunities to get back into the dating game but manages to self-destruct in humorous fashion due to his attachment to his ex. With the steadfast support of his friends, Mike is able to turn things around and get his mojo back.

50 Dates at 50 Take:

There is a lot to like about this movie, which is the Reader’s Digest version of Jon Favreau’s autobiography. Bits and pieces of his real-life experiences are mixed in with those of Vince Vaughn. This makes the scenes very authentic, since they were recreating recent life experiences.

With a budget of less than $300,000, the film had to rely on creativity and acting skill. In most cases, there was no budget for extras. The people you see at the bars, the dancers, and the band are who happened to be on location at the time of filming. The swing dance scene near the end of the movie is first-class!

The story is about the sacrifices necessary in pursuing your dreams and the damage you can do if you don’t let go of a failed relationship. We’ve all met someone who it took us a while to get past after the breakup. This movie demonstrates that once you let go and be yourself, opportunities will open up for you.

Further exemplified is how much work was involved in meeting someone new in the 90s. Back then, the only dating service was Great Expectations with their videos. We should be very grateful we have so many options available today to meet singles, especially those of us who are in the 50 Dater age group.

Why You Need to Watch It:

There are several notable scenes that men can learn from.

  • Mike’s obsession with his ex negatively works its way into everything around him. Once you have an abundance mentality, letting go of the past will be easier.
  • Mike often brings up serious subjects when talking to women he just met. This is a real turn-off. It’s imperative to keep early conversations fun and positive.
  • Mike is also so concerned about what women think about him that it blinds him to opportunities.
  • The phone meltdown scene is top-notch! I think most men have been guilty of this at some point in our lives. Mike needed to wait three to six days before making the call.
  • After finally letting go, Mike is able to be honest about who he is and where he is going. This is attractive to the right woman.
  • Trent demonstrates the most straightforward test to gauge a woman’s level of interest in a man. He asks for her phone number. He gets to it quickly and excuses himself right afterward. That’s how it’s done. Remember, guys, if she does not give it to you, it’s not likely you’ll ever see her again. So what’s the big deal? Ask. The faster you get rejected, the better.
  • Dance lessons go a long way. They teach you confidence, coordination, social skills, and leadership. I personally took them for a couple of years. You never know when they will come in handy. When you do take lessons, remember that you absolutely do not hit on your instructor or classmates. This is like trying to date a co-worker. It will lead to many awkward situations if it does not work out.
  • Mike not going for the kiss at the end of the evening with Lorraine is an excellent touch that will add some positive tension between the two when they next meet.


Year Released:  1996        Official Trailer

Swing Dance Scene

Answering Machine Meltdown Scene

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