Do you like movies starring Freddie Prinze Jr. where one of the themes involves coming to terms with the real you? No, not She’s All That. Let’s try this again. Do you like movies that have Jason Biggs and Alyson Hannigan in them? No, not the American Pie quartet. Hmmm. How about movies with Jason Biggs and Amanda Detmer where someone comes to terms with who their soulmate is? Wait, no, not Saving Silverman! We already talked about that one, remember?!? No, what I’m referring to is a classic walking-around having-a-conversation movie, but it’s not Before Sunrise. It’s a movie where Claire Forlani, the love of my life, is a woman who’s travel plans do not sync up to those of her paramour’s, but it’s not Mallrats. No, no, today we are talking about one of the most underrated romantic comedies of the last twenty-five years. We are talking Boys and Girls (2000), a sleeper that did not make back its budget. It was directed by Robert Iscove, who brought us She’s All That, but also brought us From Justin to Kelly. It stars Freddie Prinze Jr. as Ryan, a scholarly young man who insists on always having a plan and is fumbling his way through failed experiments in intimacy, and Claire Forlani as Jennifer, a woman who lives in the moment and fears being tied down to someone and all that that entails. The two meet by chance and continue to have chance encounters, becoming good friends and helping each other through their love lives until SOMETHING HAPPENS, but I’m getting ahead of myself.
I never really see this movie getting its credit, which actually surprises me because every time I watch this again, I always enjoy it. It might suffer a little bit from cramming too much into the last twenty minutes, but hey, that happens with a lot of movies worse than this that have better ratings. Another reason I love this movie, aside from Claire Forlani being in this, is it’s fascinating to see Jason Biggs, whom I despise, in a film featuring the two best romantic co-stars he’s acted alongside in his entire career (not a fan of Taylor Schilling so despite how much I love OITNB, their relationship pained me to watch, but that’s another story). Why don’t we just get into it?
We start our journey on an airplane with a young Ryan who I guess we’re supposed to think is a dork because he has glasses and braces and it’s the year 2000 and that was the sign of being a dork. A young Jennifer sits next to him telling him she just got her first period and makes him uncomfortable asking him sexual questions and questions about his parents’ marriage. They seem to automatically have that sparring chemistry that so many couples have. They argue about love but also insult each other. These kid actors are actually very solid at portraying this scene. I have a feeling this young kid is gonna out-act Freddie but, nonetheless, here we are.
We move ahead to high school years (with Freddie now portraying Ryan and Claire now portraying Jennifer) where Ryan’s school is playing Jennifer’s in their homecoming football games. Ryan is a mascot in like a chipmunk costume or something and when he hears Jennifer’s name, her school’s mascot, a fake knight, attacks him thinking he was insulting her by repeating her name. Ryan still has bad hair and braces because we need to see the contrast between him here and him as sexy Freddie Prinze Jr. It’s like a reverse She’s All That. He should know all about that. He asks Jennifer if she remembers him and she does. She invites him to coffee, and he asks about her boyfriend but she says she doesn’t have one, as she hates commitment and doesn’t want to limit herself. So, we still see the contrast between the two; Jennifer wants to be free to do what she wants not tied down to a partner, and Ryan seems to believe in a more traditional sense of monogamy. He spells it out, telling her “we don’t click” but she insists they go for coffee and he disagrees.
We flash forward AGAIN to college. Ryan is saying goodbye to his high school sweetheart Betty (Alyson Hannigan) and, lo and behold, guess who shows up? Jennifer, calling Ryan “gopher boy” and walking away as she makes him uncomfortable. Ryan is looking like a normal handsome guy but they have him in a tucked in shirt and khakis and glasses to try and make him still appear like a dork and not one of America’s biggest heartthrobs, which he was at the time.
He gets to his dorm and frees his roommate, Hunter (Jason Biggs), from a trunk he was locked inside and they introduce themselves. Hunter has frosted blonde tips and a yellow shirt on and I like the color coordination despite my loathing of Jason Biggs. Hunter tries to coach Ryan on how to tell the story of him freeing Hunter from the trunk so that he looks like a hero to women. So, Hunter is like a proto-pickup artist. Mystery probably learned everything from this guy.
At class registration, Jennifer probes Ryan about his relationship with Betty, being honest with him about the lifespan of a long-distance relationship and asking him questions about where he lives on campus, and also revealing that she has a boyfriend whom she lives with off campus. Ryan checks her on this, calling out her hypocrisy of stating she didn’t want to limit herself for love (previously) and now doing exactly that, to which she replies that it’s crazy what can happen to a person when they fall in love. Yes, Ryan, it’s called growing and learning.
We fast forward again, just a little bit this time I think, and Jennifer is upset and flipping out because her musician boyfriend broke up with her for someone else. Her friend Amy (Amanda Detmer) shows up at her apartment to console her. Jennifer goes over the detritus of their relationship, telling Amy that she found out she was broken up with by watching her boyfriend play a song live about finding someone new. Brutal! Jennifer’s top is fucking incredible. She smashes the guy’s guitar.
We cut to the library where Ryan tells Hunter that he and Betty broke up and Hunter gets excited as now they can work pickup schemes together. He tells Ryan they should get drunk and see strippers to snap him out of his heartbreak but Ryan insists it was the right move. Of course, Jennifer happens to be there too. She looks a little sad still. They discuss their breakups together and take a walk around campus. There’s that sparring chemistry again. Ryan confesses that he had an easy time dealing with the long-distance relationship, but Betty couldn’t handle it. Ryan does a flashback where he tells a story over a memory like Jennifer did with her boyfriend’s song. This is a flashback technique the movie loves to employ. Jennifer tells Ryan that the whole point of love is to surprise and drive you crazy, and Ryan says some jerky shit and she walks away.
We cut to a year later (according to the title card) and Hunter and Ryan are arguing about unhealthy relationships. Hunter’s blonde tips are now blood red and he wears red flannel pajama bottoms and a faded purple sweatshirt (solid outfit tbh) so this color coordination thing is clearly working for him. Hunter admits he can’t stop lying. It started with him trying to impress women but has become a major problem for him. Ryan says the next time he catches Hunter lying, he’ll expose him to try and rid him of his issue.
Jennifer and Amy are taking a walk and discussing Amy’s bad relationship. Jennifer advises her to just break up with the guy despite how he may feel. I admire how realistic Jennifer is about the world. Back at Jennifer’s place, Ryan shows up. Turns out he’s there to pick up Amy. So, I guess Ryan is the boyfriend she wants to break up with and Amy is the girl Hunter told Ryan he’s not in a healthy relationship with. What a small world! It already seemed like a small world when Jennifer and Ryan kept running into each other, but now we’re really narrowing things down. Jennifer is pretty surprised and informs Ryan that she’s Amy’s roommate and that Jennifer and Ryan need to talk. Jennifer breaks up with Ryan for Amy as Amy didn’t want to be the one to hurt him. Ryan leaves upset. When he tells Hunter, Hunter tells him that this is some kind of womanly test because he only speaks in pickup artist language. Hunter convinces Ryan to pretend he’s crying to get back into Amy’s good graces.
Whoa cool, Ryan and Jennifer both wear the same pair of olive Adidas sneakers. They must be meant for each other. Jennifer tells Amy how the breakup went as Ryan shows up outside. He applies balm to his face to appear to be crying but he irritates his eyes and falls down the stairs in pain. Jennifer in her amazing sleeveless sweater hoodie waits outside the health center while Ryan gets an eyepatch. They take a walk and have a nice conversation. There is CLEAR chemistry here. Meanwhile, Hunter attempts a ballet class to flirt with the women taking the class. He is dramatically unsuccessful.
Ryan takes Jennifer to a lookout spot where you can see the Golden Gate Bridge and discusses the marvel of the bridge and how good planning is responsible for it. Ryan confesses he is done with relationships and tells Jennifer she’s amazing because she just doesn’t really have a plan for after college. They flirt lightly and Jennifer apologizes for what happened with Amy. She stays to look at the bridge while he goes to do schoolwork.
The song “Happiness” by Regurgitator plays almost every time there is a scene transition and I had to look up what the song was called because it kind of sounded like a chill Smash Mouth b-side and I couldn’t place who the band was. Might have to check out more from Regurgitator tbh. We are now in the next school year and Ryan and Jennifer see each other at an extracurriculars recruiting event. Jennifer tearfully admits that she started having feelings for her summer fling but intentionally pushed him away to ensure they broke up and now she’s sad about it. She asks Ryan if he “got any” this summer and he says no. Hunter would have lied and said he had a bunch of wild orgies I bet. Jennifer suggests they get together again. We get a fun San Francisco montage where the two of them have fun together doing date activities, Jennifer pulling Ryan out of his comfort zone. They go roller blading and eat seafood and Jennifer teaches Ryan to dance at a club. Bonding! Go get married already, you two! Since this is the year 2000, everyone in the club is dancing synchronized because that’s just how clubs were in movies back then.
In some bar, Hunter, now with green tips and a really cool green and blue flannel shirt, flirts with a girl playing pool and almost ends up in a bar fight. He lies and says he’s a priest. The guy trying to fight him gets hit in the balls and Father Hunter makes a run for it. Ryan brings Jennifer home and Hunter runs by on the sidewalk. Once again, everyone just runs into each other. Ryan and Hunter leave and Hunter tries to convince Ryan that Jennifer is crazy about him, especially seeing as he rejected her offer to come upstairs. Jennifer goes upstairs and Amy has burned multiple batches of cookies while doing yoga. Amy asks Jennifer if she’s in love with Ryan or if he’s in love with her, which Jennifer denies. Jennifer insists they’re just close friends but Amy insists she’s either in love or wasting time with someone she’s not into and leaves her therapist’s number.
On another cute walk, Jennifer tells Ryan she’s going on a date and insists he should put himself out there again too. Hunter now has blue tips and a purple shirt and humongous jeans, looking like a 2021 TikTok fashion dude. Incredible. On Jennifer’s date, Ryan shows up and pretends to be her mother and insists she needs to leave because their mother is sick. She had called and asked him to come rescue her from this boring dude and she is grateful.
We see a montage of Hunter, now with purple tips, trying on like fifty different personal styles, including cowboy, Hugh Hefner and biker. Once again, I get to mention my Drunken Canal article and how Halloween costumes are necessary for personal reinvention. How does he just have all these clothes? The man owns both Lucchese boots AND JNCOs?! Amazing. This is such a menswear movie. He settles on an unbuttoned Hawaiian shirt over a long sleeve tee and goes to a party. Hunter complains to Ryan that he keeps trying to fit into the mold of what he thinks women want and Ryan asks what HE wants and Hunter admits he wants someone to love him for who he is. Ryan asks him who he really is and finds out that Hunter’s real name is Steve. He completely reinvented himself, stating that’s what college is for. Ryan says college is for defining yourself not reinventing yourself and to be himself. Steve tries to convince Ryan to talk to Jennifer before some guy she’s talking to takes her home and another woman tries to take Ryan home but he lies and says he has a girlfriend to reject her. He checks in with Jennifer before leaving, calling her “sis” and seeing she’s having fun with the other guy. Ryan seems hurt.
Later, Ryan and Jennifer are discussing her “fooling around” with a guy she got rid of by saying she had work to do. Ryan is shocked that Jennifer would have been willing to have sex with this guy if they had been able to find a condom, and is amazed that Jennifer is just willing to have sex if the opportunity arises. Once again, we see the contrast between the two as Ryan would have to meticulously plan a sexual encounter. Jennifer asks Ryan if he’s using her as a surrogate girlfriend or if they’re really friends and Ryan is hurt by the accusation and Jennifer admits that Ryan is her favorite person in the world, she just finds it weird that he isn’t sexually active or seeking anyone. He tells Jennifer about the girl he rejected at the party.
Back at the apartment, Jennifer is drinking a Slush Puppie while laying with Amy on the couch watching TV. They have a playful pillow fight and cuddle. Amy is worried about what she’s going to do when Jennifer goes to Italy after college. They end up kissing. Hands up, this was my favorite scene of the movie when I saw it in junior high. Lives rent free in my mind to this day. Jennifer is surprised by Amy trying to kiss her and Amy runs away embarrassed.
At some model bridge building class, Ryan and Steve are approached by Megan (Heather Donahue), the girl from the party who Ryan is now dating. They are all going on a double date with one of Megan’s friends and Steve admits he’s finally going to introduce someone to the real him. It actually turns out to be a triple date, with Jennifer and the guy she fooled around with from the party also in attendance. Ryan and Jennifer have obvious chemistry but not with their dates. Classic. When Harry Met Sally would be proud. Steve’s date is R&B legend Monica but playing a character named Katie who is very wholesome. Steve says a bunch of dumb shit, which I guess is the real him.
Ryan and Jennifer are going to a John Hughes film fest or something and Jennifer admits she broke up with that dude because he fell in love with her when she wanted to keep it casual. Ryan tells Jennifer he’s not really sure how things are going with Megan. He seems disinterested. After the movies, they are at some combo internet café/laundromat and Jennifer is sad and makes a speech about how there’s no such thing as true love to the entire room. She storms out and Ryan chases her and consoles her. The moment we’ve been waiting for since the plane happens and he kisses her. It’s on, baby! They go home together and we get a purple-lit pre-sex scene set to R&B music. I think this is what Tommy Wiseau was going for with The Room but just couldn’t achieve it.
The next morning Jennifer is sneaking out while Ryan is still in bed. She insists she has to go to class and he wants her to stay. She clearly wants to leave and he’s, like, in love with her. He mentions Megan and things get kinda tense and awkward. She leaves and sees Amy on the street who wants to talk about their kiss. Amy apologizes and admits she was sad about Jennifer eventually leaving but has come to terms with the fact that change will occur. They reconcile and Amy asks about what happened with Ryan, as she saw him naked in Jennifer’s bed. We see Ryan catch up to Megan to talk and cut back to Amy and Jennifer. Jennifer admits the sex was a mistake because they’re great friends and she admits she was just kind of jealous seeing him with another woman. Ryan, meanwhile, gets slapped by Megan upon admitting what happened. He goes to Steve for advice, admitting he might be in love with Jennifer, and Steve doesn’t really have much for him.
Ryan and Jennifer are out on another walk and they talk about what happened. Jennifer speaks first and implies it was a mistake and when Ryan questions her, she doesn’t pick up on his tone and thinks he’s agreeing with her. She admits they’re such good friends and it was special because he’s special to her, but they shouldn’t put too much importance on it. Ryan fakes his way through, saying he agrees with her but we know he doesn’t. He also lies and says he didn’t tell Megan. Ryan makes an excuse to leave and says he’ll call.
Some time has gone on and Jennifer is leaving messages for Ryan, who seems sad and is avoiding her. Jeez, you two haven’t run into each other yet? A sad R&B song plays. Ryan keeps ignoring Jennifer’s calls and she’s hurt that he doesn’t show up at her graduation ceremony. Later, she finally finds him at the lookout spot for the Golden Gate Bridge and presses him about not being around. She tells him she’s done with school and she’ll be gone in a few days. She asks him if he wants to do something and he says he has to get back to studying and he’ll see her around. This is PAINFUL! Grow a pair, Ryan.
Jennifer says she found out Ryan told Megan and asks him what’s wrong. He admits things are different and asks her why the sex was a mistake. He wants to know if he’s not good enough for her or if intimacy scares her. She admits she would take it back if she could because it ruined their friendship, and Ryan tries to slut shame her, saying he’s just another one of her one-night stands. He says the sex was a surprise to him, but everything became clear after and for the first time in his life, he felt alive and that everything finally made sense without any planning. The stars aligned, and not just the glow in the dark ones on Jennifer’s ceiling. He says nothing will ever hurt him more than her having the opposite reaction to the same experience. Damn. That’s heartbreaking. He admits he can’t hang out pretending nothing happened and she apologizes and admits she doesn’t know what to say. He leaves.
On Jennifer’s departure day, she has a tearful goodbye with Amy. Steve approaches and I can’t tell if he has tips or not. I think that’s his natural hair color. Jennifer asks about Ryan and Steve admits he’s in rough shape, but the shuttle driver pushes Jennifer to leave. Steve introduces himself to Amy as Steve. Seems the boy has grown! In my head this is the Sandy Perkus/Darren Silverman origin story.
In the shuttle to Italy, Jennifer talks to a woman who tells her that she doesn’t have to have everything planned out. She’ll figure out what she wants. She makes the shuttle pull over, realizing what she wants is Ryan. Awwww! Movie love! She runs to find him in his room but sees he’s gone. When she goes to her former residence, Amy is there with Steve, who tells Jennifer that Ryan is catching the 4 o’clock shuttle to Southwest Airlines to get back to LA. They are cramming every movie cliché into this ending here. I fucking love it.
Clearly this is pre-9/11 as Jennifer just hops on the plane and takes a seat in front of Ryan. She admits she loves Ryan and she’s not going to Italy. He says it’s too late, but she confesses she felt the same as he did, but he was correct in that she was scared of real love, and now is tired of being scared and wants Ryan. They discuss the fact that they don’t know what’ll happen in the future, but Jennifer admits she needs Ryan and says that while admitting that is hard, it’s easier than imagining her life without him. She says they can do laundry together, harkening back to Ryan and Betty’s breakup earlier in the film. Full circle, baby! They sit together and as the plane takes off, she helps him relax in the same way she tried to when they met as adolescents. They kiss, and that’s our movie. Oh yeah and in the end credits, Steve ends up in a dressing room with four Victoria’s Secret models. Turns out it’s a weird nightmare and he’s in therapy.
So, yeah, it may be cliché riddled. It may be easy to detect from the first scene that these two will eventually end up together. But that doesn’t make this film any less enjoyable. We get an insane wardrobe selection for Jason Biggs. We get nice, breezy chemistry between Freddie and Claire. We have a nice story with some good San Francisco scenery and even a cameo from Monica! I don’t know, I think this deserves a lot better than the 11% it currently has on Rotten Tomatoes. I love this movie. But see for yourself, it’s streaming on Paramount+ right now. You might even enjoy a performance from Jason Biggs. Don’t say I didn’t warn ya.