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2 Understanding 90s Boyfriends (and 1 Not So Much)

Being in a relationship can be a wonderful experience, but if you have your have your eyes on someone else, it can be trouble. Sometimes though, your significant other can be okay about it. Here are two classic 90s boyfriends that were pretty okay with losing the girl of their dreams (and 1 not so much).

Jerry from Liar Liar

Cary Elwes (Liar Liar, 1997)

Jerry (Cary Elwes) thinks he’s met the perfect woman. She’s smart, attractive, a good mother to a young son, and is very responsible. They’ve been dating for a short time, but he feels a strong connection. Sure, Audrey (Maura Tierney) hasn’t quite come around yet, but she’s certainly interested. And why not? Jerry is a successful professional, a hospital administrator at a very young age, handsome and willing to try and do anything to keep Audrey and Max happy (including . . . The Claw!). Yes, he moves a little too fast but he has a reason. He’s just accepted a job in Boston and wants Audrey and Max (Justin Cooper) to join him. There’s one small problem. Well, that’s a lie. One BIG problem.

Fletcher (Jim Carrey) is Audrey’s ex, a workaholic attorney with a nasty propensity for telling fibs. Thing is, he’s a generally a good guy and a great father, but he’s just not reliable and he’s too busy to be really involved with his young family. He pushed her away, even though he didn’t mean to and now he’s on the outside, trying to keep a good relationship with Max but still letting him and Audrey down with is compulsive lying. Max has had enough and makes a birthday wish that will make his dad tell the truth for 24 hours, and wouldn’t you know it, it works! Now, with no choice, and no ability to lie, Fletcher begins to see his life in a different way, and while he make a mess of everything else, it is his love for Max and Audrey that shine through.

Liar Liar, 1997

In the end, while Audrey and Max sit on a jumbo jet with Jerry, headed for Boston to look at homes, Jerry says the Three Big Words and it surprises his girlfriend. Her response to “I love you” is “thank you” and it crushes the hospital administrator, though it’s also at the moment when he sees just how dedicated Fletcher has become in saving his family. As the plane taxis for take-off, Fletcher has commandeered a motorized flight of stairs and is now pounding on the window to stop Max from leaving. That’s love. It’s also psychotic. But it’s love.

When the plane stops and Fletcher is arrested, everyone comes together and Jerry, realizing how much Fletcher means to Audrey and Max, lets her go, keeping the ticket to Boston open-ended, just in case. Talk about an understanding boyfriend. Without a hitch, he gives up and with a dour smile bids the woman he wanted to marry a fond farewell. No conflict, no fight, no fuss. That’s a nice guy.

Walter from Sleepless in Seattle

Bill Pullman (Sleepless in Seattle, 1993)

In Baltimore, Walter (Bill Pullman) has been dating Annie (Meg Ryan) for a long time and has finally popped the question. She says yes, despite some (unspoken) reservations, convinced that any relationship needs time to grow. Walter’s a very reliable guy, He’s hardworking, devoted and handsome, but he’s got a kind of a ‘thing’ with allergies. Well, not just a ‘thing’ a serious problem. He’s a mess. Sleep is basically a routine of meds, tissues, humidifiers, and wheezing. Food is like a tiger trap. You never know what’s lurking in the sauce or side dishes that will set him off. Still, he’s punctual, honest, diligent and committed. What more could Annie ask for? Turns out, a lot.

Sam Baldwin (Tom Hanks) lives in Seattle, a widower with a young son named Jonah (Ross Malinger), who wants his dad to snap out of his depression and move on with his life, though he’s not too happy with some of the dates he brings home. He’s addicted to a radio call-in show where a ‘doctor’ gives advice to people in need and calls in one night to talk about his father. Surprised by this, Sam gets lured on to the phone and confesses his feelings about his dead wife, which has half the population listening instantly falling in love with him, including Annie, who just happened to be listening to the show. She becomes obsessed with him, feeling a connection from so far away. She use her job as a journalist to acquires inside information and travels to Seattle to track him down and fall under his spells. With the classic romance film An Affair to Remember as inspiration, to make Annie and his father meet, Jonah arranges a meeting atop the Empire State Building on Valentine’s Day. Now all Annie has to do is tell Walter.

Bill Pullman (Sleepless in Seattle, 1993)

One might think that would be a hard thing, but not in this universe. On Valentine’s Day night, during an expensive dinner in a high-rise with a view of the Empire State Building, Annie confesses to Walter about Sam, a man she has yet to actually meet but feels could be the one. In real life, this is where the fight starts, a tirade of expletives about respect, commitment, communication and common decency before storming off in a rage. But Walter is not real life, and so listens patiently to Annie and with just a tinge of disappoint, smiles and says marriage is hard enough without bringing such low expectations into it. Awwww. He then invites her to go to the Empire State Building and find true love. What a good guy.

Caledon Nathan “Cal” Hockley from Titanic

Billy Zane (Titanic, 1997)

Caledon is a 30-year-old heir to a fortune in steel out of Pittsburgh. Dashing and handsome, he’s incredibly wealthy and has lived a life of ease since he was born. He sees the world divided into classes with him firmly at the top. He’s managed to claim Rose DeWitt Bukater (Kate Winslet), a 17-year-old girl originally from Philadelphia money as his fiancé, a deal brokered to ensure she and her mother, who has lost her fortune, to sustain their standing in upper society. He’s pompous, arrogant, greedy, snobbish, a bore, and wholly unlikable. Trapped in the coming marriage, Rose is depressed, and on the maiden voyage of the Titanic (also its last, spoilers), she attempts to end her life by jumping off the back of the ship.

Along comes Jack (Leonardo DiCaprio) a third-class vagabond who won passage on the trip in a poker game. He’s smart, funny, wickedly handsome and everything that Caledon is not. He’s also about the same age, and the two quickly find themselves drawn to each other, stealing away when they can to explore their newfound love and lust. Caledon catches on to what is happening with his pretty fiancé and though contends with it at first, he grows hostile, and by the time the ship runs afoul of an iceberg and just staying alive becomes an issue, he isn’t content with finding safety on a lifeboat. He wants to see Jack and Rose dead. That off the deep end angry.

Billy Zane (Titanic, 1997)

While the ship is filling with water and people are scrambling for lifeboats that are clearly not able to handle all the passengers, Caledon, so upset that his girlfriend has found someone new, he decides it’s time to brandish a firearm and shoot the lovers even though, yeah, the ocean has a pretty good shot at taking them on its own. That is one unhappy boyfriend.

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