Definitely, Maybe


The movie begins with Will Hayes, played by Ryan Reynolds, receiving his divorce papers after work, prior to picking up his daughter. Upon arriving at his daughter’s grade school, he finds the students abuzz due to the day’s introduction of sex education. His daughter suddenly has many questions, starting with how he met her mom and if he had any other girlfriends. Will reluctantly agrees to tell her the story of the three serious girlfriends he’s had. To make it interesting, Will explains to Maya that he will not tell her which one of the three her mom is and she will have to figure it out herself.  The rest of the movie jumps between the past and present.

50 Dates at 50 Take:

The film moves along quite nicely with excellent situational humor. The examples of how people leave our lives only to later unexpectedly come back are well done, especially when it comes to inconvenient timing and second chances. Some are worth pursuing, some not. The movie also does a great job of demonstrating how men are generally in way too big of a hurry, especially when trying to seal the deal and get married.

Why You Need to Watch It:

  • Typical of most men, Will is in a hurry to tie the knot. Guys, slow things down and let the relationship develop. If a woman wants to marry you, she’ll give you hints. Until that happens, focus on dating her.
  • In reality, most second chances don’t work out. Issues that caused a breakup will always resurface. The truth is we honestly only get one chance under most circumstances.
  • For most of the movie, Will does a good job of handling himself with class when things don’t go his way. His demeanor is a contributing factor to the development of second chances. The exception to this is the Drunken Confession scene.
  • April almost qualifies as the exception to the second chance. The timing between the two of them was always off: right person, wrong time. Will pretty much disqualifies himself from a second chance with his drunken confession and his pass at and argument with her. This act would be next to impossible to recover from in real life.
  • The birthday bar scene with friends is an excellent example of why you never bring up politics in a group setting or a dating situation.
  • Time can heal a lot of wounds. However, Will giving Emily a second chance after she slept with his roommate is a non-starter, even though it was years ago. Because of that event, there will always be an underlying trust issue. It’s not healthy.
  • Will’s initial relationship with Emily is why long-distance relationships don’t work out. The odds simply are not in your favor.
  • Role-playing in dating is shown to be a lot of fun here:

Year Released: 2008

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