Accomplished surgeon. Steiner patron. Midge’s boyfriend.

S2E4 - Rose overhears Edie and Ida gossipping about Benjamin, and decides to try and set Midge up with him. She becomes insufferable about it, which forces Midge to act.

S2E4: Midge interrupts Benjamin while he plays cribbage with Golda and demands that he go on a boat ride with her where everyone will see, to get her mother off her back. Josh helps the two into a boat, but Benjamin refuses to row, leaving Midge flustered and ensuring a swift return to shore. When they get back, Josh chides them for not rowing.

S2E4: Later, as the family sets up for the fireworks, Rose mentions that she was watching and asks what happened with the oars.

S2E4: That night, when the fireworks start up, Benjamin shares a smoke with Joel up on the balcony of the main building and the two discuss the concept of forgiveness.

S2E5 - After losing at Simon Says, Midge, Talia, Gabi and Eliana gossip about various things. Benjamin walks into the room and grabs a cookie, leading the topic of conversation to shift to him.

S2E5 - In the salon, Ida overhears Midge’s need to get into the city to get to work, and she says that Benjamin can drive her.

S2E5 - Benjamin drives Midge into the city. As they go, the radio gives out and Midge does an improvised comedy bit to replace it. Intrigued by this, Benjamin decides to ask her out on a date.

S2E5 - The following evening, Benjamin and Midge go to see The Legend of Lizzie. It is terrible, and they leave during the intermission. Midge takes him to see Lenny, and after the show, while he checks in at the hospital, she catches up a little with Lenny. Then, Midge and Benjamin go to the Stage Deli, where Midge admits that she does comedy.

S2E6 - Benjamin makes a surprise reappearance at Steiner on the evening of the meteor shower, and watches it with Midge. Joel looks on, jealous, despite the fact that he’s also there with someone.

S2E6 - Benjamin attends the closing night soiree at Steiner. At the bar, he and Midge arrange their next date. When Phil Foster does some standup, he exchanges a knowing look with Midge. When the dance begins, Midge initially partners with Joel, but the two soon break off to dance with Benjamin and Leah respectively.

S2E7 - Midge and Benjamin hit up the opening of a Solomon Crespi exhibit, then head to the Cedar Tavern and meet Declan Howell, who invites Midge to visit his studio the following day.

S2E9 - Benjamin attends Midge’s pre-telethon Gaslight performance, where he meets Susie. Afterwards, the two go to his place for some implied sex.

S2E9 - Benjamin surprises Midge at the park, which distresses her, because Ethan is present and she is not yet ready to introduce her kids to Benjamin. Midge learns that Rose told him where she was, and she scolds her for it.

S2E10 - At the apartment, Midge listens in as Abe interviews Benjamin because he asked for her hand in marriage.

S2E10 - Joel learns about Benjamin from Ethan, and fights with Midge about it.

S2E10 - Benjamin calls Midge from work because he hasn’t heard back from her father yet, and it’s driving him insane. Moments later, Midge gets a call from Shy Baldwin offering her to go on tour.

S2E10 - Abe finally decides to approve Benjamin and Midge’s union, but the call from Shy made Midge realize that she has to put her career first, and she tells him in not as many words that isn’t going to happen.

S3E7 - Driven by guilt, Rose comes to see Benjamin at the hospital. He reassures her that Midge was a good match for him, and he just didn’t happen to be right for her.

S3E8 - Hot off the heels of Corinne’s praise for her matchmaking skills, Rose once again visits Benjamin at the hospital, and pitches him on someone he should hook up with.

S3E8 - Assuming that Rose’s visit was arranged by Midge to assuage her own guilt, an enraged Benjamin hunts her down at The Stage Deli and vents his feelings to her.

ROSE: He's an accomplished surgeon. Lenox Hill. First in his class at Johns Hopkins. Had his choice of residencies at any hospital he chose. He's already invented new surgical techniques that have become the worldwide standard, which is a remarkable feat for such a young man. He's widely published in medical journals. Now, I know he sounds a little oddball on the surface, but he's just eclectic. That's often a symbol of accomplishment. John Quincy Adams kept an alligator as a pet. And Benjamin Franklin took naked air baths. Did you know that? I wonder if Ida's son was named after him. Oh, that's his name, Benjamin. Do you like the name Benjamin? He's never rented. He originally lived in Sutton Place - had a beautiful view of the bridge. But as close as it was to his practice, he still found it to be too far. His patients are everything to him, so he sold the place at a loss. Can you imagine that? He bought a duplex just a block from the hospital. It has views, but not of the bridge.
– S2E5

IDA: Every year, Benjamin comes to the Catskills with a box of cereal. When the cereal's done, he goes home. He had his last bowl this morning. Would you like me to ask him to drive you back?
– S2E5

BENJAMIN: It is pretty spectacular. Though “spectacular” takes on a much different meaning once a person's met you. You are spectacular.
– S2E7

BENJAMIN: Midge was right for me. I just was not right for her.
– S3E7

ROSE: You know, you won't be this handsome forever.
BENJAMIN: Well, I have a painting in my attic that would prove otherwise.
– S3E8

BENJAMIN: When you want to find a penguin, you head to the North Pole. You want to do this sitting here surrounded by your flunkies like you're the poor man's Rat Pack, or…?
– S3E8

BENJAMIN: I let you off easy, didn't I?
MIDGE: I…
BENJAMIN: You sent me a “Dear John” letter - unproofed, by the way - and I didn't chase you down, I didn't call you, I didn't show up at your door demanding an explanation, did I?
MIDGE: No.
BENJAMIN: That's right, no. I let you slink off into the night, like a goddamn Damon Runyon character. I figure if that's the way you wanted it, I wasn't gonna beg you for an explanation, an explanation I was absolutely entitled to, by the way.
MIDGE: Yes. You were. I am so sorry.
BENJAMIN: I handled the whole thing with dignity, grace. I handled it all very calmly. I handle things very calmly. I don't get mad. I can't get mad. When you're really tall, you can't get mad. You can't pace around and wave your arms in the air and raise your voice, because people get scared. See? Look around. See? That's what people look like when you're really tall and really mad. I look like an angry building! So I stay calm… all the goddamn time. But this time… (laughs): Oh. This time, you have pushed me too far.
MIDGE: What did I do? I mean, besides…
BENJAMIN: I work in a hospital, Miriam. I perform surgery. I hold really sharp tools that I cut people open with. And if I cut them open incorrectly, they tend to die. And that's where you chose to send your mother to fix me up with another girl?!
MIDGE: What?
BENJAMIN: Are you insane?
MIDGE: Benjamin, I swear, I had no idea she was gonna do that.
BENJAMIN: Bullshit, Miriam. You feel guilty. So, you decided to get me settled so you don't have to feel bad anymore. Well, fuck that. You don't get a say in what happens to me. You feel like a louse? Too bad. Live with it.
– S3E8

BENJAMIN: I am not Joel.
MIDGE: I know.
BENJAMIN: I got two feet on the guy alone.
MIDGE: You are both men.
BENJAMIN: What the hell does that mean?
MIDGE: Proud men. Strong men.
BENJAMIN: Did you ask? Did you ever say, “Hey, Benjamin, if I constantly talk about you onstage, is that a problem?”
MIDGE: No, I didn't.
BENJAMIN: That's right. You didn't even give me a chance. You left me out of the equation altogether.
MIDGE: I would have been on the road. We would have been separated a lot.
BENJAMIN: And the coming back together would've been sensational.
MIDGE: Please don't go.
BENJAMIN: You broke my heart, Miriam. Do not send your mother again. You never even got to see the ring. It was spectacular, by the way.
– S3E8

4. We're Going to the Catskills!
5. Midnight at the Concord
6. Let's Face the Music and Dance
7. Look, She Made a Hat
9. Vote for Kennedy, Vote for Kennedy
10. All Alone

7. Marvelous Radio
8. A Jewish Girl Walks Into the Apollo...

• List of Characters