It is a UK TV show called Nathan Barley featuring a character named Nathan Barley.
Thank you for clarifying. For the record, I watch a fair number of UK programmes, but have never heard of this one. There are others like the original UK The Office where mentioning someone like David Brent would be less puzzling. Still, can we make a point of mentioning the show as well as the character name?
Scott Pilgrim in Scott Pilgrim vs. the World was the first to spring to mind (and I love that movie dearly), but now I want to got a bit broader and say “anything starting Michael Cera”
Rebecca Bunch from Crazy Ex-Girlfriend.
Forrest McNeil from Review, though his cringey awkwardness is more on the “earnestly clueless” end of the spectrum.
Andy Dick’s character Matthew in Newsradio.
He was plenty awkward on Arrested Development, but hardly a patch on Tobias Fünke.
Yes, even the UberEats ad! “Small bites.” 
Rupert Pupkin. The King Of Comedy (1982)
Elspeth in Elspeth.
Dabney Coleman played basically the same repugnant character in three sitcoms, Buffalo Bill, The Slap Maxwell Story, and Madman of the People. Each of them took the character Coleman played to perfection in 9 to 5 and threw him at us each week. Many critics admired Coleman’s performances in the three shows, but audiences didn’t. Coleman tried another show where the character attempted to become a better, less obnoxious person, but that failed as well.
Anything with Jerry Lewis.
I would give A MILLION DOLLARS to be able to see that show again. I loved it so much that I would just quiver with delight throughout entire episodes.
I will nominate Sarah (aka Titicaca) from Absolutely Fabulous. She got worse (more cartoonishly awkward) in the later years of the show, but she was always somewhat cringy. (She was played by Naoki Mori who has range: she was Miss Sixpence in Topsy Turvy and also a regular on Torchwood.)
Bob (Bill Murray) in What About Bob.
That’s an odd one. I remember watching the original Ricky Gervais version and being frequently so horrified that I clutched a pillow to my face shouting “No, no shut up.” Despite this David Brent managed to end up a clueless but sympathetic character. When I eagerly started watching the US version I found Michael Scott to be simply cruel, repellent and unlikable so it never worked for me.
Nathan Fielder playing Nathan Fielder in anything that he has ever made is a difficult but very funny watching experience.
Doc Martin from Doc Martin.
Not too cringey, but definitely awkward.
Finally making out with the woman of his dreams, followed immediately by suggesting she might be suffering from gastroesophageal reflux disease.
Smooth.
Well, Don Knotts made a career out of playing cringy and awkward characters on comedy TV and in comedy movies, so there’s that. Examples would include Mr. Furley on “Three’s Company” (TV) and Roy Fleming in The Reluctant Astronaut (movie).
Eugene Levy in the American Pie movie series.
These characters are certainly awkward, but I wouldn’t call them cringey.
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Moss is an idiot savant, and perfectly happy in his own little world.
Dougal is an innocent idiot, and is similarly unperturbed by reality.
Stuart from the (IMO, underrated) HBO series Hello Ladies. (Played by Ricky Gervais’ longtime collaborator Stephen Merchant.)