By: Victoria Edel
Everyone knows I am a Nora Ephron romcom stan. As Boyfriend Month draws to a close at GPG, I found my mind wandering to the many men Nora gives us in her three iconic romcoms — When Harry Met Sally, Sleepless In Seattle, and You've Got Mail. We never actually see the three male leads — Harry, Sam and Joe — as Meg Ryan's boyfriends, since the movies end when they get together. But there are other boyfriends in the movie who we do see. So here is a ranking, from worst to best, of the many love interests and boyfriends of the Nora Ephron-verse by much I would like them to be my boyfriend.
8. Joe (When Harry Met Sally, Steven Ford)
Joe — Sally's boyfriend near the beginning of the movie who drops her off at the airport — just gives us nothing to work with. I mean, this guy is so uninteresting that I had never even googled the actor who played him before; apparently, he was the son of US President Gerald Ford, which is weird. Joe knows Harry from work, and he drops Sally off at the airport, and Sally is upset when they break up. We find out later that he didn't want to get married, but then he calls Sally to tell her he's engaged to a paralegal named Kimberly, who he just met. That alone is terrible behavior. Obviously I've only been an adult during the Internet age, where you find out about exes getting engaged because of Instagram, but I assume in the '80s, the mechanism wasn't that different — your friend finds out your ex got engaged and then they break the news to you gently. It's absurd to call your ex to let them know!! It's cruel to call an ex who wanted to marry you, but you told them you never wanted to get married! Fuck Joe.
7. Walter (Sleepless In Seattle, Bill Pullman)
Poor Walter, the man who never had a chance. Long-time readers know this a pro-Bill Pullman newsletter, but Walter truly gives us nothing. He has a cold, which dooms him immediately even though all of us have also had colds. Probably the biggest point in his favor is that he's extremely chill when Meg Ryan breaks off their engagement for a man she's basically never met. I assume Walter marries some nice, also boring woman and they have three kids and are pretty reasonably happy in the Maryland suburbs.
6. Frank (You've Got Mail, Greg Kinnear)
Ranking Frank is hard. For many reasons, he kind of sucks. His brand of hipsterism was kind of cute and quirky in the '90s, but by the 2000s there would be legions of guys like Frank complaining about the internet and being annoying about typewriters. He flirts with Parker Posey in front of his girlfriend (I do not blame him, but still, not great behavior), and shows his girlfriend a tape of him on a talk show where he also flirts with the host. Rationally, Frank should be even lower on this list.
And yet, I cannot dismiss him. Greg Kinnear is extremely handsome, for one. When a woman shushes him in a movie theater, he says, "A HOTDOG is singing. You need quiet while a hotdog is singing?" which personally I would like to put on a tee shirt, as someone who has been shushed during the commercials before a movie. Frank and Kathleen have maybe one of the nicest breakups of all time, and isn't the sign of a good boyfriend someone who would be nice to you after a breakup? I would date Frank, and maybe he would annoy the shit out of me sometimes, but I think it would be mostly be pretty good.
5 Harry (When Harry Met Sally, Billy Crystal)
I love Harry. I love him! He loves to go out and do things. He loves to bitch about people, which is also one of my favorite past times. I, too, always flip to the end of a book to see what happens on the last page. And yet, I worry that Harry would be too negative for me. We would drag each other down. Sally isn't a negative person. When Harry makes catty comments, she tells him to stop being bad, even as she smiles and laughs. They even each other out. I believe Harry and Sally are extremely happy together, but I think Harry would not make me as happy as some other people on this list.
4 Joe Fox (You've Got Mail, Tom Hanks)
Listen. Listen. I know so many of you hate Joe Fox. I know. And yet!!! The hold this man has on me!
Obviously the biggest issue is that Joe's family company, Fox Books, makes Kathleen's bookstore, which was her inheritance from her late mom, go out of business. Maybe if I had seen this movie for the first time in the '90s, I would be madder about that aspect. But in modern America, Fox Books would be the one going out of business, and Kathleen's bookstore would keep chugging along! That makes me feel less bad about it. I mean, we're living in a time where we are nostalgic for Barnes & Noble.
I saw a letterboxd review of You've Got Mail that said Joe and Kathleen basically fall in love while writing Nora Ephron essays for each other, which is true, and maybe that's what I love about Joe so much. He's sharp and funny. He knows his life is kind of ridiculous. He is incredible sweet to the children in his life. He reads Pride & Prejudice because Kathleen tells him too, and I believe he loves it. Also his speech to Kathleen before she goes to meet her Internet friend (who is really him) about how he would have asked her out the moment they met, and they would never fight over what movie to rent, and he's just so sorry and can't she just find it to forgive him — ugh. It kills me. Slays me. My favorite. So yes, I know you, reader, would probably not want to date Joe Fox. But I am a weak woman. Wreck my life, ruin my nights!
3. George (You've Got Mail, Steven Zahn)
Technically George isn't anyone's boyfriend or love interest in this movie, but I think he's quite wonderful and would be a great boyfriend. He's a little eccentric, but in fun ways, not annoying ones. He really loves books, especially children's books, which is hot. It's like how I'm attracted to all men who teach early childhood education. He takes his bookselling job very seriously, even when he moves over to Fox Books, where they don't have as rigorous standards. He is respectful of all his women coworkers, and they like spending time with him in their free time. Also, I recently watched That Thing You Do and they make a lot of jokes about Steven Zahn not being cute, and I was offended by that. Steven Zahn is cute!
2. Sam (Sleepless in Seattle, Tom Hanks)
The pangs of emotion I just felt looking at photos of this man on Google...whew. I used to be a Sleepless In Seattle hater until our own Hayley made me see the light, but even when I wasn't a fan of the movie, I was always a fan of Sam. I mean, that's the premise — that this man is so wonderful that it makes sense for a lonely woman in Baltimore to lightly stalk him. But watching Sam with his son? Watching him slowly deal with his grief and his son's grief? His connection with Meg Ryan? It's all perfect. He also has the number one romcom job, architect, which is the perfect combo of creative and practical. I would happily move to Seattle to live on a house boat with this man and his amazing child.
1. Jess (When Harry Met Sally, Bruno Kirby)
Jess! For most of When Harry Met Sally, we don't really know anything about Jess, except that he's Harry's kooky best friend who loves to make fun of him and serve as his sounding board. They go to sports games together, get into shenanigans in a batting cage (classic romcom trope), and go for an iconic walk in the park.
And then, at one fateful dinner, Jess meets Marie (Carrie Fisher). And he just knows, right away, that this is it. This is the love of his life. Within a year, they're living together and walking down the aisle. Maybe if someone did that in real life, I would be a little worried, but there's a steadiness and certainty to their relationship that's just instantly there. Jess is not the type of guy who is going to lead you around. When he is in, he is 100 percent in.
When Marie and Jess comfort a post-coital Harry and Sally (pictured above) and hang up, Marie says to him, "Tell me I'll never have to be out there again." Jess, with such certain, easy joy in his heart, wraps his arm around her and says, "You' will never have to be out there again." Nora Ephron has maybe never written a more romantic line.
Honorable Mention: Paul Child (Julie & Julia, Stanley Tucci)
Paul Child, the husband of Julia Child, was a real person, so we can't really give Nora Ephron any credit for his creation. BUT he rules so much, and Stanley Tucci does a fantastic job portraying the deep, abiding love between Paul and Julia in Julie & Julia, and I say that as a Tucci-anti. If their dynamic at all interests you, I really really recommend reading Julia Child's memoir My Life In France, which just overflows with the love the pair shared.