One of the highlights of my time at theological college was a set of lecture courses given by Dan Strange on contemporary culture and apologetics. The fruit of his labour were recently shared with the wider world through his short book, Plugged In: Connecting Your Faith With Everything You Watch, Read and Play. 
In this excellent book Dan encourages Christians to follow four steps in our engagement with our culture in whatever shape or form we encounter it – all modelled by the apostle Paul in Acts 17:
Entering: Stepping into the world and listening to the story: ‘For as I walked around and looked carefully at your objects of worship…’ (Acts 17: 23).
Exploring: Searching for elements of grace and the idols attached to them: ‘People of Athens! I see that in every way you are very religious. For as I walked around and looked carefully at your objects of worship, I even found an altar with this inscription: To an unknown God’ (Acts 17: 23).
Exposing: Showing up the idols as destructive frauds: ‘Therefore since we are God’s offspring, we should not think that the divine being is like gold or silver or stone – an image made by human design and skill’ (Acts 17: 29).
Evangelising: Showing off the gospel of Jesus Christ as ‘subversive fulfilment’: ‘So you are ignorant of the very thing you worship – and this is what I am going to proclaim to you' (Acts 17: 23). 
I want to suggest that when it comes to our response to the increasingly prominent experiences of transgender people, most Christians have rushed to attempt step three without bothering to do the necessary groundwork of steps one and two. The result is that our words and actions too often show that we don’t really get the painful experiences of those who genuinely experience gender dysphoria. We consequently fail to effectively connect them with the hope of the gospel (step four).
We need to find ways of entering into the lives of those who feel their experienced gender identity is different to their biological sex. Some of us will be able to do this in conversation with family members or friends – sensitively asking them to share their experiences with us. Others will need to turn to documentaries, blogs, books or other media that chronicle the experiences of trans men and women. Books that have especially helped me include:
Jan Morris’ Conundrum (Faber & Faber, 1974) – One of the first published accounts of a transition from a male to female identity.
Thomas Page McBee’s Man Alice: A True Story of Violence, Forgiveness and Becoming a Man (Canongate, 2014) – The story of a move from a female to male identity.
Juno Dawson’s The Gender Games: The Problem with Men and Women…from Someone Who Has Been Both (Two Roads, 2017) – An account of a gay man’s embrace of a female identity.
It is only by entering into the hearts and minds of real people created in God’s image that we can properly start exploring the mixture of grace and idolatry at play in their lives. To give just one example, in The Gender Games, Juno Dawson movingly shines a light on the damage gender stereotypes do to many children (giving most Christians much to repent of) but then goes on to demonstrate an idolisation of a certain narrow vision of femininity as she shares the story of her transition from identifying as male to female. This conundrum (to borrow Jan Morris’ book title) needs careful exploring if we are ever to share the gospel effectively with someone like Juno.
Motivation to do the hard work this will involve comes from Paul in Acts 17, but also from Jesus himself. In the mystery of the incarnation he graciously entered our world, explored it in a body like ours, exposed our idolatry, and seeks to evangelize us all, and he does this in ways that so often speak personally into the particular pains of our lives.
 Daniel Strange, Plugged In: Connecting Your Faith With Everything You Watch, Read and Play (The Good Book Company, 2019).
Strange, Plugged In, p.119.