- Actor Allusion: In the Season 2 episode "A Stray Dog Walks Into a Bar", Brett tells Candance she has a face of a Disney star. Appropriate considering Bridgit Mendler's previous show.
- Dyeing for Your Art: Between the penultimate episode and finale of season 3, Bridgit Mendler dyed her hair red. It's only brought up during the Cold Open of the finale. Justin is said to be bothered by red hair, because the first time he caught his father cheating on his mother, his father was dressed as Ronald McDonald.
- Enforced Method Acting: Executive Producer Bill Lawrence says that various actors are secretly given lines (usually fourth-wall-breaking take thats) that the rest of the cast don't know about in order to get genuine shocked reactions while broadcasting live.
- In a scene where Charlotte has to shock Candace, Whitney Cummings showed Bridgit Mendler a photo that was so surprising, Mendler let out a genuine shriek and had to break character to take another peek at the photo before recoiling in shock a second time.
- Production Posse: An unusual example with Briga Heelan. She was cast in both Undateable and Ground Floor when they were in pre-production but chose to stick with Ground Floor while her role in Undateable was recast. Then production hiccups led to Undateable being delayed and the producing teams of the two shows both wanted Heelan badly enough that they worked out a scheduling agreement that allowed her to return to Undateable and take on the role of Nicki on a recurring basis. Both of these shows are executive produced by Bill Lawrence.
- Rory Scovel, Harvard from Ground Floor, appears in one episode and Robert Maschio from Scrubs as a very brief cameo in another.
- Brent Morin has since guest starred on Ground Floor as a rival of Mansfield's.
- Briga Heelan returned in Season 2 with Rene Gube. Their characters were engaged like they are in real life.
- Zach Braff, Donald Faison, Neil Flynn, Christa Miller and Sarah Chalke have also all made apperances.
- Real Life Writes the Plot: Almost immediately before the third season's premiere was supposed to go on air, Rick Glassman hurt his tongue badly enough to require several stitches. Because of this, Bursky is practically silent for several episodes and only started getting more than a sentence to say once Glassman's tongue healed enough for him to speak comfortably.
- Screwed by the Network: Undateable was given a summer burn-off with very little promotion from NBC and was absolutely savaged by critics. Surprisingly, it caught on with audiences and did very well for a summer series. Enough for a renewal, albeit with a slightly shortened second season.
- Sleeper Hit: The show was critically lambasted, dumped into the 2014 summer season with little promotion, and burned off (see Screwed by the Network), but it didn't just do better than expected. Not only was it winning its time slot, it also had the strongest summer premiere out of all the Big 4 networks in 5 years, and increased its audience during its first run.
- The second season's live episode generated so much buzz that the show was renewed for a third season with all live episodes.
- Throw It In!: The cast likes to ad lib to crack each other up and keep the Studio Audience fresh. These ad libs are frequently included in the final cut, complete with Corpsing and the Studio Audience's raucous reaction.
- According to Bill Lawrence, the cast tries to stick with the script as much as possible for the East Coast feed, but then cut loose and go after one another for the West Coast feed.
- The 3rd Season premiere's East Coast feed was almost completely derailed when Bianca Kajlich decided to go off script and plant a kiss on TV's Scott Foley. The rest of the cast struggled to keep it together (David Fynn actually had to run off set) long enough to finish the scene.
- Whitney Cummings threw in a dick joke that got Chris D'Elia, who has a reputation for never breaking out, to crack up. He managed to collect himself enough to strike back and bring the house down with "Don't get us canceled TWICE!"
Trivia / Undateable