Much like his fiancé, Shoshanna, we only just met Byron, which might be his biggest appeal. Other than the fact that he shares Shoshanna's (and every sane person's) affinity for a good cupcake kiosk, all we really know about him is that he has fancy friends and has apparently made Shoshanna realize how toxic her own friends are.
Whether he's guiding Hannah through her cocaine adventure or offering to father her child, he's always been there for her. Having been drug-free since we've known him and rocking the single dad thing since his baby mama left, we know he's dependable.
So maybe he's a little bit of a pushover and slightly obsessed with Hannah. There are worse flaws.
Scott was a young entrepreneur who had a thing for Shoshanna when she was at peak selfishness. She gave a really bad interview but he fell for her anyway. His only crime was falling for her at the wrong time... and maybe going into the soup industry.
Joe was the perfect coworker at the perfect job, but leave it to Hannah to screw up perfection. He even brought her home one night when she was drunk without making it creepy. It's not quite clear if he was into her but she definitely accused him of it - although, they definitely share the same taste in plaid.
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Likely the most underappreciated boyfriend on the show, the actor who played Charlie (Christopher Abbott) exited the show due to behind-the-scenes disagreements with Lena Dunham. Although this meant his story was left unfinished, he returned recently after losing his father and becoming a drug dealer who lives in a seedy apartment.
Still, during his two-season run, he was too good for Marnie. While making her a table inspired by something he saw at Restoration Hardware, he learned that she felt smothered by his love. Then when he got another girlfriend who makes artisan mustard and he started his own lucrative app, she came back along to shit all over everything once again.
George was a good boyfriend and an even better sugar daddy. Although his actual son was horribly homophobic, he was willing to put Elijah up in Hannah's spare room. What he wasn't willing to put up with was Elijah having sex with a woman.
He may have gotten sloppy drunk at parties and had bad judgment in younger men, but he seemed like a sweet guy.
Right off the bat, Fran wasn't here for Hannah's crap. The teacher with an affinity for shirts of literary icons could have been good for Hannah, if only she was ready for it. Instead, she had him leave her at a rest stop, and tried to give Ray a blowjob.
Perhaps he was just to naïve to think she could handle a serious adult relationship. It also didn't help that he was kind of boring.
Although we only knew Yoshi for a short time, he seemed like a fun date. Shoshanna's workplace crush in Tokyo, he took her to a sex club which she seemed to enjoy. They might have been perfect for each other if she had stayed in Tokyo.
This handsome older man had a good job, a nice brownstone, and a sauna. Although it was a bit sketchy to have a two-day affair with a random woman who hijacked his trash cans, he seemed well-intentioned. Having recently divorced, he shared a deep connection with Hannah in a short amount of time. Then she cried, and things got weird.
This guy who went to high school with Hannah had a certain small-town charm, and he seemed oblivious to her pretentious nature. He was also the heir to his dad's pharmacy. When he gave Hannah some free lube for her menopausal mom, we went weak in the knees.
His only fault was that he was a bit vanilla in bed, if not a little slut-shamey. Then again, most would be caught off guard by being asked, "Am I tight like a baby?"
Ray has always been a know-it-all, and he seemed to lack motivation for a while. But he was a perfect first boyfriend for Shoshanna as they helped each other grow. His worst judgment may have been starting a fling with Marnie, who never appreciated him.
Donald Glover's two-episode run as Sandy had a lot of potential. Unfortunately, he came across as the token black boyfriend, which isn't his fault. However, the fact that he was a republican was just unforgiveable.
Oh, Adam. For one, it's not cool to shack up with another woman in your ex-girlfriend's apartment, especially when you haven't even officially broken up. Also, don't shack up with said ex-girlfriend's best friend.
Although he attempted to come to the paternal rescue when he learned that Hannah was pregnant, we're too smart to pretend a baby would solve anything. He used Hannah for way too long and ultimately, their whole relationship was toxic. Whether it was his addiction or her OCD, they were constantly depending on each other.
Hannah's Montauk fling was just a chill surfer enjoying the beach and the babes. Taste aside, he was good to Hannah during her trip. We can't even blame him for having a girlfriend since they apparently had an understanding. He could have been a bit more helpful with the souvenir he left in Hannah's womb but he reacted just how she expected him to, even if it felt kind of shitty.
When we first met Thomas-John, he was a one-percenter living in Brooklyn and trying to weasel his way into a threesome with Jessa and Marnie. He was also super sensitive about his white rug.
Soon, he jumped the gun by getting married to Jessa during her quarter-life crisis. Although he failed to defend her to his parents and ultimately called her a whore, both parties seemed to be hurt. Perhaps he'd make a better husband to a completely different kind of woman.
This hottie who went to camp with Shoshanna was ready to get hot and heavy during a movie date. Although he was totally pro-cunnilingus, it was his fear of her hymen that sent him running. He wouldn't have lasted much longer anyway.
Although we want to love the gay character, he's a constant reminder of what we hate about being gay. On top of that, he gave Hannah HPV when he was experimenting with heterosexuality. He also cheated on George with Marnie.
But just like the others, he's grown over the years. He even helped Hannah's dad acclimate to the gay scene. And perhaps his budding Broadway career will be a new start.
Dill could have been perfect for Elijah. A rare steady relationship for our gay protagonist, this Anderson Cooper-esque character was an ideal boyfriend and apparently great in bed. But he ultimately left poor Elijah heartbroken.
He also recently returned as a racist father-to-be. Not cool, Dill.
Booth was a narcissistic artist who loved to make girlfriends out of his assistants, or perhaps vice versa. He came off as really sexually aggressive in the most inappropriate times, even though Marnie locked herself in her boss's office to finger herself over it. Ultimately, he was too much in love with himself to be with anyone else.
Pal was a typical mean gay who vacationed in the Hamptons with a then-estranged Elijah. After leading Elijah on and being kind of a dick to him, he went to Marnie's first performance (after that whole Kanye cover) just to point and laugh.
Desi was much more into drugs and drama than music. Although this has helped many artists in the past, it just seemed to sabotage everything he touched. Having left Marnie high and dry too many times, he's just become a burden.
Zachary Quinto's short appearance as Ace had us disgusted with him for the first time since that Tori Spelling show. He had an oddly toxic friendship/sexual tension with Mimi-Rose, the woman Adam left Hannah for without telling her. Ace also strung along Jessa who was very vulnerable at the time. But the worst offense of all, he walked around with a toothbrush in his mouth like it was a cigarette.
Jasper's only purpose in returning to Jessa's life was to completely derail it. An old friend, he came back to pull her off the wagon right after she'd gotten clean. He was a symptom of her daddy issues at their worst.
In one episode, this literary hero of Hannah managed to disgust us all. He spent a majority of the 30 minutes convincing her that he shouldn't have to feel guilty for having sex with his fans. And just when they manage to make a meaningful connection, he puts his dick on her without warning.
Jeff was the cliche deadbeat dad. An unemployed musician who depended on his super successful wife (played by Kathryn Hahn), he tried to get into nanny Jessa's pants.
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