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For those who have grown up like me in the 2000s watching rom-coms, Justin Timberlake’s character from Friends with Benefits looked like one of the biggest red flags. We saw him avoid commitment, keep things casual, and end up hurting the woman who genuinely loves him.
However, when I rewatched it again yesterday, my perspective changed. Was Dylan really the bad guy we thought him to be? Sure, Dylan isn’t flawless, but Jamie, aka Mila Kunis, isn’t completely the innocent one either. After all, didn’t they both willingly sign up for a no-strings-attached arrangement?
Later, when feelings start creeping in, Dylan seems determined to pretend that almost nothing has changed. Eventually, their carefully planned arrangement turns into an emotional mess. But can we really blame only Dylan for all this?
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Did Justin Timberlake’s Character Dylan Really Lead Jamie On In Friends With Benefits?
Before you dump all the blame on Dylan, there’s one thing you need to remember: Jamie wasn’t forced into this arrangement. In fact, in the rom-com movie, we saw both characters getting tired of their complicated relationships and finally agreeing to keep things only physical. They made the rules together, and neither promised the other a romantic future.
And, for a while, their plan seemed to work out in the most perfect way. Dylan and Jamie enjoyed each other’s company, joked around, and developed a date-like friendship. However, the more time they spent together, the harder it became to pretend that their connection was purely physical.
But when Justin Timberlake, aka Jamie, visits Dylan’s family in Los Angeles, their relationship starts to get more serious. She gets to see his personal life, bonds with his family, and discovers his vulnerabilities. However, things take a bad turn when Dylan tries to downplay his relationship and tells his sister that he’ll never date Jamie because of her emotional damage.
Sure, that’s a red flag, and I’ll not sugarcoat it. Dylan knew about Jamie’s insecurities and is now using them against her. Jamie has every reason to feel betrayed. But I’d like to remind you here: Dylan never entered their arrangement pretending to want a serious relationship. His biggest mistake, however, was acknowledging that the relationship had changed.
Was Dylan’s Fear Of Commitment Hiding Something Deeper?
While Dylan’s romantic decisions are questionable, Friends With Benefits shows us another side of his personality through his relationship with his father. Played by Richard Jenkins, his father was living with Alzheimer’s disease, and seeing his father lose his memory may have taken a toll on Dylan too.
Throughout the movie, he tries his best to hide his vulnerability behind jokes. However, his family life shows that he isn’t as emotionally detached as he wants to portray. One of the most important moments comes when Dylan spends time with his father at the airport. Dylan’s father recalls a woman he loved but let slip away, and that regret never went away.
This makes Dylan finally confront his feelings. It takes his father’s regret to help him realize that maybe always playing it safe isn’t the best option. And finally, we get a cheesy, romantic rom-com ending. But even though Justin Timberlake’s Dylan isn’t a red flag, I couldn’t really put him in the green flag category either. Maybe he just had the best and worst of both worlds.
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