Everyone who knows me personally knows that I am a major movie buff.  I once pursued a career in the feature-film industry in the late 1980s and most of the 1990s.

I have a ‘love-hate’ relationship with most of the romantic comedies and dramas that premiere each year.  I hate watching a movie that deals with dating and relationships that seems highly unrealistic or too “romantic fantasy” oriented.  On the other hand, I love romantic comedies and dramas that include characters and storylines that are very realistic and relatable.

One such movie in the latter category is Malcolm Lee’s 1999 romantic comedy / drama, The Best Man.  The movie stars Morris Chestnut, Monica Calhoun, Taye Diggs, Terrence Howard, Sanaa Lathan, Nia Long, and Harold Perrineau.  The movie centers around the week leading up to the wedding between NFL football star Lance Sullivan (Chestnut) and his fiancée, Mia Morgan (Calhoun).  Sullivan’s best friend and designated best man in his wedding is Harper Stewart (Diggs), who is an up-and-coming book author and novelist.  Stewart’s most popular book is a novel that is partially based on his real-life friendships and his personal interactions with women in his life.

In this article, I will highlight each character and what you can learn from them.

HARPER STEWART (Actor Taye Diggs)

Harper is the best friend to Lance Sullivan since their college days.  Lance was a popular college football player, and Harper wrote for the college newspaper in the sports department.

Harper is a man who is more so into long-term romantic relationships with women, but he has also had his share of short-term erotic trysts with women.

The biggest secret in the movie that Harper is hiding is that he engaged in sexual activities with Lance’s fiancée, Mia while they were in college.  Neither he, or Mia, has ever confessed this to Lance, but Harper indirectly mentions this tryst with Mia in his novel, with all the names changed into fictional characters.

Lesson to be learned from Harper’s character:  Sometimes, the girlfriend, fiancée, or wife of one of your best friends may develop an emotional bond with you, and even go as far as to offer you her sexual companionship.  I have had this happen in my life at least a handful of times, and at least once, I actually did engage in sex with the girlfriend of a friend of mine (unlike Harper, I did not keep it a secret … I confessed this to him days later).  This is an awkward position for any man to be in, and the best thing to do is never allow yourself to become too close to the romantic companion of one of your close friends.

JULIAN MURCH (Actor Harold Perrineau)

Julian is a classic example of a henpecked boyfriend.  His girlfriend, Shelby (Actress Melissa De Sousa), is very controlling, bossy, manipulative, and spoiled and Julian simply does not have the backbone to stand up to her high maintenance ways until the very end of the movie.

Lesson to be learned from Julian’s character:  You can never allow your female companion to heavily control and influence your behavior, and generally dictate the terms of her relationship with you.  The woman will eventually lose respect for you and move on to a man with more confidence and backbone (or at minimum, she will regularly cheat on you behind your back with a man who is more ‘Alpha’).

QUENTIN (Actor Terrence Howard)

Quentin might have been the most hilarious character in the film.  Quentin had a very dysfunctional relationship with his mother, and consequently, he is very wary of the manipulative and sexually duplicitous ways of most women.  He is a sworn womanizer, he is very anti-monogamy, and he is always on the lookout for his next sexual conquest.

Lesson to be learned from Quentin’s character:  Every man – particularly those who are very naïve and inexperienced with women – need a close friend like Quentin.  Quentin is the one who encourages Harper to be honest with Lance about his one-night stand with Mia; Quentin is the one who encourages Julian to develop some backbone with Shelby; and in one of the most powerful scenes in the movie, Quentin is the one who enlightens Lance about the sexually duplicitous and untrustworthy tendencies of many women.

LANCE SULLIVAN (Actor Morris Chestnut)

Lance is a classic example of the type of man I refer to as an “Alpha male with a few Beta traits and tendencies.”  If you read my article from last week, I touched on how many men can be just as duplicitous as many women are.  There are some men that have promiscuous tendencies, but when they meet a woman who they believe is ‘The One,’ they will give that woman the misleading impression that they are the most faithfully monogamous man on earth.

When Lance was in college, he was a cheater and a lying womanizer, frequently engaging in sex with his many football groupies behind his girlfriend Mia’s back.  Little did he know or realize, Mia was well aware of Lance’s cheating ways.

Lesson to be learned from Lance’s character:  If you are a man who frequently cheats on your long-term girlfriend, fiancée, or wife, make no mistake … there is a 90-99% chance that your significant other knows about your infidelities.  Furthermore, there is at least a fifty percent chance you’re your significant other has someone – or HAD someone – ‘on the side’ herself.  As they say, what is good for the goose is good for the gander.


When choosing a romantic comedy or drama to view, always seek to watch those films that have characters and storylines that resonate with you and that you can learn some morsels of wisdom from.  I have a long list of movies that have provided me with both entertainment, and helpful enlightenment.

More about Alan Roger Currie can be found on Wikipedia.org; Visit Currie’s main website to find out more about his Email consultations, Skype & Telephone consultations, and One-on-One / Face-to-Face Coaching sessions.  Currie also has an active YouTube channel where he offers his own unique brand of knowledge, wisdom, insight, and general advice related to dating and relationships.  If you are a single heterosexual man, and you want advice on how to develop the confidence and courage to be more upfront, specific and straightforwardly honest about your sexual desires, interests, and intentions with women, check out Currie’s eBooks, paperbacks, and audiobooks.  Currie has been a featured speaker at many dating advice workshops for men in the United States as well as internationally.  If you want to become a Patreon.com subscriber of Dating Coach Alan Roger Currie, CLICK HERE