Mike
In season 4's "Twaining Day," fans are introduced to Mike, a handsome and friendly EMT. His and Abbi's meet-cute is the result of an embarrassing injury sustained at her workplace, Soulstice. In the following episode, "Just The Tips," Abby and him wake up together and that's where things take a turn.
Mike notices that Abbi has a strand of his chest hair stuck in between her teeth, and while the embarrassing moment is mild, it's still extremely awkward.
Adele
It's a match made in heaven when Ilana meets her perfect match: Her doppelgänger, Adele, played by Alia Shawkat (Arrested Development). At first, it's not apparent to Ilana that her new love interest looks exactly like her, making for a fun set up.
In the end, the pair realize that despite the mutual attraction, their stances on lifestyle choices are too different to continue seeing each other. It's not that this a bad date, per se, but it is unfortunate that the two couldn't see eye to eye.
Will
Technically, it's their second date, but this is the first time viewers meet Abbi's significant other, Will. In season 1's "Destination: Wedding," Abbi and Ilana, and their former co-workers spend the episode racing to make it to a mutual friend's nuptials in Connecticut.
Abby brings Will as her plus one, but things go off the rails when the group has to embark across town to Penn Station. Will ends up ditching her, and needless to say, it's the last time fans ever hear of him.
Lesley
During season 5, Abbi starts seeing a doctor by the name of Lesley (played by Clea DuVall). While it's exciting and important to see her explore her sexuality, their romance never fully reaches its potential due to their differing levels of maturity. Lesley believes that Abbi is not grown up enough to handle the responsibility of an adult relationship.
Although this experience forces Abbi to re-examine her life and grow as a character, it's sad to see Lesley not accept her for who she truly is.
Male Stacy
One of Broad City's most prominent guest appearances comes from Seth Rogen playing Abbi's love interest, Male Stacy, in the second season's premiere, "In Heat." Their first date takes place in the middle of a New York City heatwave in Abbi's sweltering apartment.
What transpires is a sweaty evening that eventually ends in Male Stacy passing out. Although the two appear to be compatible and get along well, this date is just too hot for all the wrong reasons.
Tyler
In "Stolen Phone," viewers are treated to a wild trek across Manhattan as Abbi attempts to track down her missing phone. Meanwhile, Ilana meets Tyler, who is suspiciously perfect. Abbi's mission gets delayed when Tyler invites the friends to come out and watch him perform with his improv troupe, Statutory Crepe.
It turns out, Tyler's brand of comedy is painfully problematic and humorless, which makes for a truly uncomfortable experience.
Trey
For the first couple of seasons, Abbi's Soulstice boss, Trey (Paul W. Downs), is annoying and unlikable. So, it's a big surprise later on in the series' when the two start hooking up. Abbi, out of embarrassment, hides their budding relationship from her best friend. Everything comes to a head when Abbi and Trey end up going on their first date to the same restaurant where Ilana is celebrating her parent's anniversary.
Although fans see a tolerable side of Trey on this date, their relationship is toxic from the get-go as it threatens to create distance between Abbi and Ilana.
The DJs
Broad City never shies away from talking about sensitive and personal matters. In episode 5 of season 1, "Fattest Asses," Ilana and Abbi meet a pair of smarmy DJs played by Matt Jones (Mom) and Jason Mantzoukas (Big Mouth). Their questionable behavior eventually escalates to the point where it ventures into concerning territory.
Although the episode is full of humor, it also makes a points out the importance of consent and trusting ones' instincts.
Mr. Miller
When Abbi matches with her former high school english teacher, Mr. Miller (Mike Birbiglia), on a dating app, things take a turn for the worse. After taking Ilana's advice, Abbi invites him to the ritzy brownstone where she is housesitting. When the two reunite, they both admit to, at one time, crushing on each other.
From then on, the date quickly becomes even more inappropriate and creepy as Abbi soon realizes that they're better off keeping things in the past rather than the future.
Jeremy
Broad City excels at subverting viewers' expectations and in "Knockoffs," the series masterfully dodges a "will they or won't they" romance between Abbi and her neighbor, Jeremy. Things seem to be going well on their first date until Jeremy asks her to perform an intimate act. Although she consents, it results in the damage of a "possession" and exposes an immature and condescending side of her crush.
This will go down as one of the series' most memorable episodes, and it's no wonder seeing that it's chock full of the series' signature brand of cringe.