Travis (Ryan Merriman) and Lena (Kayla Ewell) have been dating for a while and Travis feels ready for the next step and goes out to buy a beautiful and expensive diamond ring. But then the bad luck starts to hit as he is let go from his sales job, his writing career is going nowhere and his brother, Cedric (Adam Korson), is less than supportive when it comes to Travis trying to grow up. Despite this Travis plans to take Lena away on a glamping trip so he can propose, except nothing goes as planned as they bump into an old boyfriend of hers. And then Lena drops a bombshell, she has been offered a position at a prestigious medical program in Munich.
I hate it when I watch a movie and after it has finished wonder what the point was. That is sadly the case when it comes to "How Not to Propose" as it just doesn't seem to know what it is or where it is going and that leaves you with the what was the point feeling. What I mean is on one hand we have Travis trying to propose on a glamping weekend but nothing goes to plan, unfortunately it struggles to be amusing when things go wrong. And then you have Lena secretly conflicted between love and a job offer in Munich. The two never comes together with the supporting characters, Travis's man child brother who is a video gamer and Lena's pushy mother, just adding to the misery of the failing humour.
In truth whilst the casting of Kayla Ewell and Ryan Merriman is a plus point with the actor's likeable nature making "How Not to Propose" watchable the whole TV movie feels like everyone involved was just going through the motions. It certainly doesn't manage to stand out from the crowd of easy to watch romantic TV movies and ends up patchy with it only occasionally hitting the sweet spot of being entertaining.
What this all boils down to is that sadly in comparison to other TV movie's "How Not to Propose" ends up forgettable and a bit below par with it never really flowing.