Review: Cupid (comedy web series) – will you fall in love with it?

Cupid is an award-winning web series from Posh Dinosaur Productions. It is co-written, directed and performed by Michael James Dean and is all about Ben, an awkward recently-made-single guy trying to get back into the dating game.

Winner of the DigitalMation Awards 2015, and nominee for London Digital Film Festival, Rio Web Fest and Miami Web Fest, this is a series with way fewer views than it deserves. We watched it through, and here’s a blow by blow account of what we saw.

Episode 1: Looks straightforward enough. Ben is trying to make a video for his online dating profile, a simple twist on the classic comedy trope of awkwardly trying to leave a message on an answering machine. The episode seems to be following that path – all the distractions, retakes, and accidental slips into telling the truth, that you might expect.

It’s deftly done, and pretty watchable, but it’s building up to something much more intriguing. The cliff hanger ending is a good hook to make you reach for Episode 2.

In Episode 2 we meet the eponymous Cupid, played by Darren Ruston, and the chemistry between him and Ben is reminiscent of a good extended Mitchell and Webb sketch. Though the concept is pretty far-fetched, the naturalistic style of writing and performance, allows us to suspend disbelief, since the characters are behaving as you might expect if this stuff happened in real life.

If something’s unbelievable, you can bet that one of them is not believing it. It’s shot well and has enough post-production effects to give the impression of a grander budget. Another teaser ending, entices you to stay tuned.

Originally these shows were broadcast monthly. Series one is all online, so you can binge watch it, Netflix style.

Episode 3 is a pretty decent send up of the meat-market that dating often becomes, and attempts satire of certain modern character flaws. You can tell that this series is written by men, though, as the female characters, though recognisable and sharply realised, seem less believable.

Of the potential dates on offer, one of them is pretty outrageous and would be on the wrong side of offensive if it wasn’t for a sympathetic performance all round, and a fairly ambivalent attitude to them from the writers. Again, the episode is leading to a tangential pay-off, which is nothing to do with playing the dating game.

Episode 4 has a lot of heart. Shelley Davenport as Keyleigh lights up the screen, and the warmth of the writing and performances is delightful. There is a little reliance on cartoon humour, but when it’s used it helpfully drives the plot and characters.

While the show seems to be following a classic story arc here, there is enough novelty in the set up to keep it fresh, and you can’t help but think they’re not going to be that predictable.

In Episode 5, Ben is on a first date with Lucy. Given how he chooses to spend it, and given how the apparatus of modern dating has been dissected in previous episodes, you start to get a sense of how the writers feel dating ought to be. As a sitcom, of course, nothing is allowed to go completely as planned. In sitcoms you’re always one outrageous character away from something awkward.

By this point, the series has settled into a rhythm of tight 6 minute episodes, which pass by in a flash and leave you wanting more.

Episode 6 and Ben agrees to let Cupid join him and neighbour Kayleigh on an afternoon out. The fact that a lot of the action in this series happens in afternoons and mornings gives it a wholesome feel.

The characters may swear, and we may be heading towards some of the more intimate corners of the dating experience, but the decision to keep things light, adds a classiness to the whole production. As it is, the characters seem more aware of their feelings than their urges, another testament to the maturity of the writing.

Even Cupid, often the cartoon character, shows a charming depth. The outlook of the series and the journeys the characters are undergoing are nothing new, but they’re done well. Even the occasional blasts of CGI work as this series heads toward the final acts.

Episode 7 claims to be a true story. The tone switches from the angst of dating to what happens when human bodies collide. The episode title “Frenulum” may well be something of a spoiler, but again, it’s all in the delivery. This doesn’t go the way you might expect, and while it plays with sex, kinks and everything messing up, it manages to portray “sexy times” without seeking to titillate.

Episode 8 is in two parts. It’s a few months later, and Ben is at a party, struggling with his insecurities by trying to brag his way out of them. Cupid deals with the lack of alcohol in his system by finding something stronger. Ben betrays feelings that he’s not even prepared to admit to himself and as things fall apart around him, he allows his inner selfish child to take charge.

Given we’ve been seeing the series through his eyes so far, this is the episode where we stop being on his side. A strong performance from Shelley Davenport as Kayleigh, closes the deal on this thoughtful interlude in the story.

Episode 9 and the cast are really in the groove. Cupid can be entertaining by just eating a sandwich – in fact that’s the first 30 seconds of the episode. Once the conversation gets going, it’s home-truths all round as Ben and Cupid come to blows.

Music plays a good role in setting the tone of this series, with an attitude that’s wistful without being mawkish.

As we reach the climax of series one, Episode 10 is a bumper 20 minute special. Ben’s at a party, and has found proper dickhead to talk to, which shows him for the nice guy he really is. With a new credit sequence and the longer format, this installment looks a little like a show-reel for Posh Dinosaur Productions themselves. The longer format allows the show to breathe, making it seem less like an extended sketch on a single subject.

It seems that the characters have moved on a long way since the low point established in the previous episode with both Ben and Cupid getting new jobs and focusing less on their problems. Though all the characters have gotten on with their lives, it seems that old feelings are not entirely in the past.

In a rather self-aware sequence, the gloom is transformed to optimism as we remember the moments from previous episodes where we were rooting for the characters to follow a more conventional love story, and Cupid seems to be working the magic that his name suggests. A beautifully shot scene in a church provides a distinctive climax to the series, which never allows for the expected to happen.

Even though a longer format, the editing, direction and attention to detail mean that the time flies past. The episode even manages to make a passing reference to another Posh Dinosaur Production – Already Dead.


Though it has its imperfections, and though the drama is relatively gentle in pace, this series is well worth watching. We can’t believe how few views some of the episodes have. At its best, it’s a slickly produced, thoughtful, inventive comic drama with a lot of heart. Where it descends into more crudely drawn humour, it’s never gratuitous, and where it uses well-kn0wn tropes from situation or romantic comedy, there’s always something extra to wrong foot you and keep your interest.

The fact that the show works in the longer format they used for episode 10 shows the potential it has for development into something bigger.

Watch it now

Start with Episode 1 – below, or visit


Enjoyable Thoughtful, inventive comic drama with a lot of heart

About Amber ShowSpot

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At ShowSpot we cover Comedy Shows, Videos, Reviews & have plans for much more so watch this space! Amber is a comedy fan, Fringe-goer and nerd. Finding the funny since 2003.

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