Top 5 First Date Movies
Entertainment Movies

Top 5 First Date Movies

With romances blooming all over, there comes that important moment of the First Date. Where do you go, what do you do? I can’t count the money in your bank or pocket so what I can do is offer some advice if your bank account is not date ready. Stay at home, invite her over for a movie. But be careful how you do it. Nowadays Netfilx & Chill means something else than coming over to watch a movie.

There has been plenty of love stories to hit the theaters over the years but only a few have stuck out in my mind. I have not seen every “chick flick” but as a man who’s secure in his manhood and has been married before, trust me when I tell you that I have seen my fair share of some. Some I loved, some I didn’t understand and some I was left wondering why the hell that was made. I have my favorites and these are the 5 that I will recommend for movie night with that special someone.

Ladies, if you want to know if he is the right one for you then press play and see if he yawns or grabs his phone. Fellas, if you can sit through one of these then you must have some feelings for her. And if you happen to like the movie, don’t feel bad as I did in the beginning, embrace it. It will be well worth it in the end.

Lets begin with The Top 5 First Date Movies

Love Jones: (1997) Larenze Tate, Nia Long

Love Jones is the classic case of “Boy meets girl, loses girl, then gets her back”, but in between were some of the best sex, romantic scenes ever put on film. It has all the cliche’s as most romantic movies does but there were other elements involved that made this one of my favorites. Yes, Nia Long was and still is beyond sexy in this movie but the onscreen chemistry between her character Nina and Larenze Tate’s character Darius was outstanding. Guys joke other guys all the time about what we will do for women to get attention but Darius had possibly the smoothest approach in any movie to get Nina’s attention. He said everything to her without saying anything to her with a poem.


Dinner and dancing lead to one of the best next morning scenes in the film. Nina wakes up to Darius cooking breakfast (mind you this is not his home, so you know she put it on him). They fit in well in each other’s circle of friends but a truly romantic movie could not a call itself that without a few twist. Nina, listening to her friend tries to do a mind trick on Darius and go spend time with her ex-hoping that Darius would proclaim some love for her and tell her not to go. But Darius not wanting to overplay his hand brushes off the situation and in the process loses Nina.

Once gone, he does what all men do and women think we don’t do. He punked up and starts whining to his best friend Savon about what drove her to leave. While Nina is away he finds another woman, but Nina returns and catches him in the act and decides to get a little payback by dating his friend Hollywood.

Yes, this really goes on in life.

They rekindle, break up again and then we are hit with the scene of him racing through the train station only to miss the chance to tell her how he feels. Did they make it in the end of the movie? Of course they did, right?

The reason I picked this movie over the countless others I have seen is the pure genius of the writing. This was 20 years ago when men were taught to think with the smaller head other than their heart. Ego was the downfall of Darius and security of the heart was the downfall of Nina. Neither wanted to give in until it was too late.

Love & Basketball (2000) Omar Epps, Sanaa Lathan

“Double or Nothing”

With that line, we had our ending and everything afterward was just icing on the cake.

As a sports writer, I am a bit biased when it comes to this movie simply off the basketball reference alone but the story line was great. The basketball scenes not so much but you can’t win them all.

Quincy and Monica grew up together as next-door neighbors, both with a deep love for the game of basketball. Quincy is the son of an NBA player and Monica is the daughter of a banker but somehow they find each other amidst the chaos that goes on, on the court and off. It starts off with them as kids then skip to senior year in high school as their feelings for each other grows but both are still in denial. But Prom Night changes everything and this is where we as viewers start to reminisce about our high school/college love and you forget the rest of the characters and focus on Q and Monica and their fight to stay together or apart depending on who you are rooting for.

Quincy was the star while Monica was the backup and she was comfortable with that as long as her role in Q’s life didn’t change. But when Q’s dad dropped the bomb on him that he was unfaithful to his mother everything in his life changed including his devotion and trust in Monica. While his stock began to fall on the court her’s started to rise and his ego took a bruising in the process. But he wasn’t alone in his self-guilt trip as Monica started to focus more on basketball which resulted in a powerful scene in the film when he confronted Monica outside of her dorm and told her he was dropping out of school and going pro.

“You forgot to be there”

As years passed, Monica would become the star on her college team and overseas while Q became just another bench player for the Los Angeles Lakers. Quincy injured his knee, which caused him to come to terms with his basketball immortality, confront his estranged father and dealt with his own misgivings in life. On the flip side, Monica’s playing days are over and she moves back home with her parents to work in her dad’s bank. In an encounter with her mother Monica is asked if she is going to Quincy’s wedding, where her mother calmly tells her that Quincy could do better in which she was referring to Monica.

Then comes the scene that puts most love stories climax to shame.

I love this movie because it sums up so many relationships. We all get caught up in our own world that we tend to forget about the person that we have shared the good times with and alienate them when we are having bad days. Trust was never an issue with Monica and Quincy it was the outside world they let come between them and destroyed what was once an unbreakable bond since they were kids. They eventually got the bond back but they had to separate to find themselves in the process.

Pretty Woman (1990) Julia Roberts, Richard Gere

The classic “Cinde- F****** rella” story but with a twist.

I love this movie, this is one that my mother took me to in my younger years and I didn’t understand the significance of it until I got older and had to make decisions about the type of woman I wanted in my life.

The movie is about a rich business man who by chance meets a hooker named Vivian walking the streets of Los Angeles. We find out in the first few minutes that he is beyond spoiled as he spent an incredible amount of money on a car he can’t drive, pays women to pretty much stay out of his life and rents the penthouse suites at hotels even though he is afraid of heights. Classic rich spoiled life but she is here to turn it upside down.

From the beginning, it was pretty obvious how it was going to turn out in the end as this was the 90’s when conventional was mandatory, unlike today where one of the lovers will end up hit by a car or dies of some fatal disease. Those times were all about the romance and Pretty Woman delivered.

I knew she was a prostitute but I never brought her as a prostitute. She had a back story as to how she became one and as she spoke you could see the ice start to melt from his heart. Their first night together was summed up by this line “I’m a safety girl”. After all these years I still remember that. There was the no kissing rule, the strawberry and champagne, and the wig. Few knew who Julia Roberts was but when you saw that red hair as she slept on the bed, I know for me I was sprung on her, still till this day.

With Edward having to be in town for a few more days for business he needed a companion to accompany him on business dinners and when suggested by his friend and business partner Philip, Edwin, with the voice of Prince screaming from the bathroom had a plan.

“How much for the week?”

Just like that, a romance was born without either knowing. He thought he was getting paid arm candy and she thought she was getting legendary status on the streets by reeling in the big fish.

You ever heard the phrase “you clean up nice”?

That was the night everything changed in their business deal. It became a relationship without the Yes, No or Maybe box.

Everyone wanted to know who she was, especially his business partner who when he did find out decided to take a stab at her. In to save the day came Edward with the weakest punch in movie history and protect his investment.

Big fight and Viv splits, heads home to begin packing to get away from the life when she hears the music.

I chose this movie as it shows that when a man or woman can put away their pride and not focus on one’s past magical things can happen.

Definitely Maybe (2008) Ryan Reynolds, Isla Fisher

I know Pretty Woman is the most famous out of two but this movie here, man. If you have children then this is a family must-see, even if you’re going through a divorce, child support battle or you just don’t like one another. I’ve never asked my mom how she met my dad, but I’m pretty sure it’s not as romantic and self-reflective as this movie was.

Will is going through a divorce, when on one of her visits his 11-year-old daughter, Maya wants to know how he met her mother. Seems like a simple question but instead of giving her the I bumped into her at a coffee shop, we locked eyes and that’s the end he sent her on a scavenger hunt of sorts with clues. To make it more interesting he changed the names of the women to confuse the poor child.

Will started in the political world working on a campaign for then Governor Bill Clinton where he was already in a long distance relationship with possible mother Emily but that in turns go sideways. Left single, he and his best friend Russell open their own consultant firm after Clinton is elected and he hits he dating world. He and possible mother April become best friends but you can see the sexual tension oozing off the two but they stay platonic while dating others.

He then meets third possible mother Summer, who is friends with first possible mother Emily but she is in a relationship with some old horn dog. Will is not having the best luck with women and to top it off his best friend April is now dating a new guy and he is left alone until he receives an invite to a book reading from the horn dog. He finds out Summer and he is no longer dating and a relationship is sparked. Summer writes an article for the guy Will and Russell is consulting for and love is in the air. Maya knows for sure that Summer is her mom but noting is as it seems with the story.

Problems arise and Will and Summer breakup, their business sinks and Will becomes a slob. April is in love with a new guy, and all the while telling this story poor little Maya is beginning to hate every women she hears about forgetting that one of them could possibly be the one that gave birth to her. April drags Will out for his birthday where he makes amends with everyone including Russell but he skips out in the middle where April finds him and they have a falling out when Will confesses his love for her.

No Summer, no April, no Emily and poor Maya has no idea who her mother is until he tells Maya how he bumped into Summer who invited him to a party where he had a conversation with Emily but yet deep down still yearned for April. At that moment, Maya knew who her mother was.

For those that haven’t seen the movie I can no longer go into detail about how it turns out. I will have to end it here.

I picked this movie due to the creativity of the script. This is a writers dream, to have the audience guessing, as he had his daughter guessing right until the end. Other than the creative writing process this was a story about a man who had it all in the beginning, lost it, found it, lost it again while all the while the right love was having to come to terms that he was in love. Men tend to fight that urge and Will wanted it so bad that he forgot he had to be willing to sacrifice in the process.  If you have kids, especially a daughter, as a man this is a must see. I often wonder how I would tell my story if she ever asked.

The Notebook (2004) Ryan Gosling, Rachel McAdams

I don’t care what your skin tone is, if you seen this movie then you understand why it’s #1 on my list.

Where Definitely Maybe succeeded The Notebook exploded. It began with Duke telling a story of two teenagers caught in a summer romance, one poor and the other rich. The female, Allie at first was not too thrilled about the young brash Noah but the first date, or shall I say the first lay in the street put her heart in a whirlwind. Noah knew from the beginning she was the one.

Not all was great, it was still young love so there were fights and arguments but in the end they managed to work it out. Towards the end of the summer it was confirmed that Allie was to leave and head off to school and back to the real world but thinking with her heart she wanted to stay and be with Noah. Noah, who didn’t want to hold her back fought with her or should I say Allie fought, slapped, yelled and cried but Noah was determined to break up with her.

The next morning she was gone and Noah tried to move on with his life. He and his friend Fin joined the Army, where tragedy struck but during his time he wrote Allie everyday for a year. Allie was off living her life, engaged to be married until she came across a local newspaper with Noah’s picture.

She packed up some clothes and told her fiance she was heading out-of-town to handle some business (that’s code for fling). She arrived in Seabrook and headed straight to Noah’s. There was a silence, then “Hello”. Noah just stood there and watched as she tried to get in the car and drive off, eyes still gazed as she almost ran the car into a ditch.

Over the next few days there was awkwardness, silence, laughter, fights and one really weird dinner between Noah, Allie and his new love interest. There was still an elephant in the room between the two and Allie couldn’t hold in any longer.

“Why didn’t you write me? It wasn’t over for me. I waited for you for seven years”

Summer romance my ass.

Duke continues to tell the story of a two torn lovers of how they met, broke up, met again and ultimately had their fates tied to each other in the end.

The Notebook is my #1 romance movie for many reasons. The energy it gives out it astounding. The message it sends is that true love never dies.

Honorable Mention

Titanic (1997) Leonardo DiCaprio, Kate Winslet

I would love to put this movie on my top 5 but for a few reasons I will have to leave it off.

It was entirely too damn long. By the time you finish watching this you will have broken up.

It was a nice love story but the ending ruined it for me. Happy endings are the way to go in Hollywood and in life we look for those. How are we supposed to have some cuddle time afterwards when we are asking our significant other what would they do if there was supposedly room for one on that piece of wood?

The movie made you think too much about life and death when you should be thinking about the next date.

And the last reason it’s not on this list is because Rose was heartless and I don’t want my woman seeing that any getting any ideas in her head if we were put in a life or death situation. The main reason I don’t do boats.

So forget you Titanic and your First Date crushing movie. Great movie if you’re already in a relationship but not for a first date.

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Mark Wilson
Mark began his writing career for Yahoo then Rant Sports before deciding to head out on his own at TruluvSports. Now, he is lead NBA writer as well as co-owner of Inscribermag. His topic ranges from sports, Lifestyle, Sex, live streams and more. Mark's work has been featured in Sports Illustrated, ESPN, Bleacher Report, Fox Sports, MSN, Yahoo Sports and many others. No one is perfect but he does his best to provide fans with an honest opinion and not the saturated, watered-down sports and news everyone dishes out.