Ways of the Womanizer in Film

There was a time when womanizing was all part of the allure and appeal for some women, with some believing they might the one to tame a playboy of his ways.

Over the years, this lifestyle continues to appeal to some men, and trainers, dating coaches, and pick-up artists (PUA) have been there for us since.

Such adventures aren’t for all of us, and Hollywood seems to return to this formula every couple years, suggesting the womanizer is a hit at the box office. We just have one question. Are these suitable first date movies?


The “date doctor” helps clients learn new tricks, and woo the women of their dreams.

Crazy, Stupid, Love

When a middle-aged woman asks her husband for a divorce, he seeks to rediscover his manhood with the help of a newfound womanizing friend and learns how to pick up girls at bars. This one is a must see.


For Hollywood to come up with a bigger womanizer than Frank T.J. Mackey would not be easy. Not just a pick-up artist (PUA) but also the creator of “Seduce and Destroy,” a system to help men with manipulating women into having sex with them. Tom Cruise provides one of his best performances in this film, whether a fan or not, it’s worth a watch.

Ghosts of Girlfriends Past

While at his brother’s wedding, a serial womanizer is haunted by the many ghosts of his past girlfriends.


A womanizer in NYC learns some lessons the hard way, while leading him to question his behaviour, loneliness and priorities.


Now this is one with a twist. A sex-addicted con-man that is trying to pay for his mother’s hospital bills plays on the sympathies of those who rescue him from choking to death.


If there is one womanizer that needs no intro, its Casanova.

While there’s numerous others, like James Bond, Tony Stark of Iron Man, and Bruce Wayne of Batman, we went for less than super heroes and secret agents and more with regular guys. Did you know Robert Downey Jr., who plays Tony Stark in Iron Man, also played a character named Jack Jericho in The Pick-up Artist several years before. True story.

But we couldn’t end this without mentioning Chazz Reinhold, the womanising man-child from Wedding Crashers.

While John Beckwith & Jeremy Grey (Owen Wilson and Vince Vaughn) played a couple of lady killers, it was Chazz that was especially notable.

If you’re more likely to live your life vicariously through others, you might want to watch the movie The Change-Up as it might be what you’re after.

Also See:

Playboys and Casanovas – Living Large

How to Sell Yourself With a Pickup Line

How to Woo Women with a Pickup Line

The Insiders Guide to Dating – How to Find Happiness

About Max

Single and sexy. Hello ladies..

About Max Green

Single and sexy. Hello ladies..