True Crime Documentaries to Watch on a Date

Picking a documentary for a date is a small test of taste. Too grim and the mood sinks, too light and there is nothing to argue about. These five are about cons, cold cases and the people who chase them, and each one leaves plenty to talk about afterwards. Where to watch changes by country and by month, so check a streaming guide for what is available to you.

If you want to talk about red flags

The Tinder Swindler (Netflix, 2022, directed by Felicity Morris, 114 minutes) follows Shimon Hayut, an Israeli man who presented himself as the son of a diamond mogul, used Tinder to meet women and persuaded them to lend him money he never repaid. It is a surprisingly good film to watch with a new match, because it is really about trust. Everyone has a theory about what they would have spotted first, and you learn a lot about someone from the answer. Try asking, “At what moment would you have walked away?” The people in it are real victims, so save the jokes for the plot twists and not for them.

If you like a stranger-than-fiction twist

The Imposter (2012, directed by Bart Layton, 99 minutes) is about the 1997 case of Frédéric Bourdin, a French con artist who posed as Nicholas Barclay, an American boy who had disappeared in Texas in 1994 at the age of 13. Bourdin was seven years older than Barclay and had a French accent, brown eyes and dark hair, yet several officials and family members accepted him. The film mixes interviews with dramatised scenes, so it plays like a thriller. It is a great pick if you enjoy shouting “how did anyone believe that?” at the screen.

If you want to watch the scammers get chased

Love Fraud (Showtime, 2020, four episodes, directed by Heidi Ewing and Rachel Grady) follows private detectives, including bounty hunter Carla Campbell, as they search for Richard Scott Smith of Lenexa, Kansas. Several women accused Smith of romance scams, and he is accused of having been married at least ten times. Four episodes make it an easy weeknight binge, and it opens a useful chat about staying safe while dating online. Ask each other which warning signs you would want a friend to point out.

If you want a slow-burn mystery

The Jinx: The Life and Deaths of Robert Durst (HBO, 2015, six episodes, directed by Andrew Jarecki) looks at three events: the 1982 disappearance of Kathie Durst, the 2000 killing of Susan Berman and the 2001 death of Morris Black in Galveston, Texas. Durst was suspected in the first two. In the third he claimed self-defence and was acquitted. The finale made headlines because Durst was arrested the day before it aired, which makes this a good pick for two people who like to pause and compare theories.

If you are in a serious mood

I’ll Be Gone in the Dark (HBO, 2020, six episodes plus a special in 2021) is based on the book by Michelle McNamara, who researched the Golden State Killer and died before she finished it. The series follows her work alongside interviews with detectives, survivors and family members, and covers the investigation up to the arrest of Joseph James DeAngelo. It is the heaviest of the five, so save it for a date when you already know each other’s limits.

How to make it a good date

Ask before you press play. Some people avoid stories about violence against children or animals, and it is much better to find that out in a text than on the sofa. Pick one episode, not a whole series, and pause when something sparks a conversation. Talk about the cases with care, because every one involves real people. And if either of you wants to stop, stop. There will be another night, and another documentary.