There are some shows that I expect to rip my heart out and stomp on it: Bojack Horseman, This Is Us, cable news. Freeform’s The Bold Type is not one of them. The series is my security blanket.
As a fellow writer in women’s media, I relate to Jane (Katie Stevens), even though her job at Scarlet requires way more vagina facials and sex parties than mine. I want the best for the more-than-slightly neurotic, but ultimately scrappy “tiny Jane,” and against my better judgment, I even shipped her and reformed player, author, and former Pinstripe columnist Ryan (Dan Jeannotte). Yes, Ryan kissed another girl at the end of season 3, but he told her immediately! And if Jane could get over Ryan’s drunken, yet fairly chaste betrayal, then so could I.
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That is, I shipped these two until The Bold Type pulled off a twist so heartstopping, I literally spit out the cupcake I was eating at a midday snack (don’t judge me, we’re observing social distancing).
At the end of Thursday’s season 4 episode “5, 6, 7, 8,” Jane’s previously recurring sex dream — in which Ryan stands outside the door wearing scrubs and tells Jane she can “leave when she’s ready” — returns. It is odd, because the last time she had this dream, it was over the fact that she couldn’t fully trust Ryan after he, a millennial Jay McInerney, admitted to kissing a girl while on his whirlwind book tour. Also, his book was about sleeping with half of New York City. No judgments, but clearly Ryan was staying on brand.
Jane and Ryan, however, have seemingly worked out these trust issues. Sure, Jane kissed a rando at a sex party to level the playing field, but mostly, Ryan has been a great boyfriend this season. Only episodes ago, a concerned Ryan took Jane to her doctor’s appointment after she found a lump in her breast, then played hooky with her to get her mind off the situation. He doesn’t deserve a medal, but it’s clear he loves and cares about Jane. He’s reformed! His cad persona only exists within the pages of his book!
In Thursday’s episode, it initially seemed that this dream returned because though Ryan did not cheat on Jane again, he did lie to her. In the previous episode, “Stardust,” Jane’s brother Evan (Chord Overstreet) comes to town, and Ryan learns that he and his wife are splitting up before Jane does. Evan tells Jane about the breakup shortly after, but Jane still questions why Ryan didn’t beat him to the punch.
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A fair question on Jane’s part, but I’ll admit: I also understand where Ryan was coming from. Evan only told Ryan his secret after Ryan saw Evan kissing someone who was not his wife, leading Evan to explain himself immediately. Breaking Jane’s brother’s confidence didn’t seem like the right move, even if it meant waiting to tell Jane the truth.
By the end of “5, 6, 7, 8,” however, I regret ever having given Ryan the benefit of the doubt. Jane returns home after a conversation with her boss Jacqueline (Melora Hardin), having had an epiphany about what her cryptic sex dream was trying to tell her.
Is Jane a psychic?!? Potentially! She confronts Ryan and, for the first time in months, asks him what really happened with that girl on the book tour.
Reader, he had sex with her and lied to Jane about it the entire time. Cue the cupcake.
It’s in this moment that I realize Ryan’s not just a dude who effed up: He’s someone who made a calculated decision not only to cheat on his girlfriend, but to attempt to win back her trust by lying to her about the severity of his betrayal. This whole time, as he promised to work harder to be the boyfriend she deserved, Ryan was making sure he had the best possible chance of being forgiven for his actions, even though Jane never really knew what she was forgiving him for.
It’s a heartbreaking twist, but maybe one that The Bold Type needed. Things tend to work out for Jane and besties/co-workers Sutton (Meghann Fahy) and Kat (Aisha Dee). Hell, in the first episode of season 4, the trio broke into a printing company, stole a copy of a since-pulled Scarlet magazine issue, had that copy stolen from them and published on The Cut, and still managed not to get fired. Jane botched her Forbes interview for the “30 Under 30” list and still managed to earn a spot. Sutton, once broke, was able to live on a fashion assistant’s salary thanks to her wealthy soon-to-be husband.
Things working out for The Bold Type ladies is part of the reason I like the show — it’s comforting to know that, despite the dramatic bumps along the way, things will probably be just fine. In life, things aren’t always that simple — and now, Jane sadly realizes that, too.
Ryan, I was rooting for you. We were all rooting for you.