‘The Bold Type’ Season 2 Reunites Pinstripe And Jane In Episode 4

“The Bold Type” is bringing back a familiar face. Pinstripe, also known as Ryan, will run into Jane in Season 2, episode 4, and Jane will spend plenty of time with her former fling.

To recap, Pinstripe (Dan Jeannotte) worked at a men’s magazine as a sex columnist in the same building as Scarlet. He and Jane (Katie Stevens) started hooking up and he even gave Jane her first orgasm last season on “The Bold Type.” However, Jane wanted a serious monogamous relationship, and she decided that Ryan wouldn’t be able to give her that. She broke up with him shortly before he was laid off from his job.

In Season 2 of the Freeform dramedy, Jane will run into Pinstripe at a café where she can barely afford the biscotti. The sneak-peek video above reveals that Pinstripe is still wearing his duds from the night before. He’s a gossip columnist now, and he’s getting paid to party.

Employed Jane may have looked down on this job. After all, she left her dream job because she wanted to be a serious political reporter, and she lost her new gig because she didn’t want to tear a woman down. However, Unemployed Jane is real desperate. She thinks she could be a gossip columnist too. She just needs a little guidance from her ex.

In another video clip, Jane proves that she might have a talent for this when Pinstripe takes her to a bar. She asks Pinstripe what his strategy is, and she learns that he has to wait for a good opening because he’s a guy. Jane, however, can walk right up to the intended source and learn who he’s here with. Jane discovers that an athlete, who already has an Adidas endorsement deal, is hanging out with a Nike representative. It looks like she’s got her first story.

Jane wants to keep this professional, though. After all, she has a hot new doctor in her life. She’s still seeing Ben (Luca James Lee), but there might be some trouble in paradise after Jane realizes that the doc has some very different personal beliefs. Her sudden issue with Dr. Ben and her renewed friendship with Pinstripe makes Sutton (Meghann Fahy) wonder if Jane has herself a love triangle.

Find out when “The Bold Type” Season 2, episode 4 airs Tuesday at 9 p.m. EDT on Freeform.