May The Road Rise Up To Meet You (2026) Review – A Different Kind of Entanglement

A young trans man finds himself in an entanglement with a married woman.

ByAmari Allah Hours Posted on

[Unless Said Otherwise] Spoiler Alert: This summary and review contains spoilers.

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“May The Road Rise Up To Meet You” Film Details

Movie Summary

Malik, a 23-year-old trans man, meets Deena at the bus stop for a secret rendezvous. But how much longer this secret could go on is anyone’s guess – especially as Deena wants to control when and how the two meet up.

Cast and Characters

  • Malik (Joy Matthews)
  • Deena (Fiona Mwaka Callan)

Review and Commentary

Highlight(s)

A Messy and Toxic Relationship [82/100]

The short starts by making it clear this relationship isn’t sunshine and rainbows, so seeing the good times shift to bad is both entertaining and appalling. You have an older woman, with a family, seemingly taking advantage of a young trans man, but at the same time, it isn’t like Malik doesn’t know about Deena’s family.

But as much as the short’s description tries to present Malik as an equal, you see over time that isn’t true. He might be able to get Deena off, using their sexual chemistry to balance their relationship, but Deena counters by deciding when and where they meet. In addition, she always has the fact that she is married in her back pocket, so when things get serious, she can shut things down.  

Then, when that doesn’t work, she goes so far as to misgender Malik. The short leaves you wondering what Deena sees in Malik: his youth and appearance, or someone she assumes will be vulnerable and willing to keep their relationship secret. Either way, he becomes a temporary escape from her marriage.

This ultimately leaves you to wonder if Deena is an example of gender not making a person less capable of being selfish or manipulative, or whether she is simply a terrible person?

Overall

Our Rating (82/100): Positive (Worth Seeing)

May The Road Rise Up To Meet You, with its complex mix of love, lust, and power dynamics, leaves you questioning how you should see Deena and how responsible Malik is for continuing the affair, even as Deena holds more power.

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Amari is the founder and head writer of Wherever-I-Look.com and has been reviewing media since 2010. He approaches each production with hope, rooting for every story to succeed, and believes criticism should come from unmet potential, while praise is reserved for work that meets or exceeds expectations.