Dynamic Watchlist Hub: Apr 19, 2026

10 Best Movies Like Sleepless in Madrid

If you loved Sleepless in Madrid, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for Sleepless in Madrid.

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#1
Love & Sex

Love & Sex

2000‱★ 6.1

Why watch this? A perfect follow-up to Sleepless in Madrid for fans of Drama & Comedy & Romance. It captures a similar light-hearted atmosphere.

When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of th...

#2
Walking and Talking

Walking and Talking

1996‱★ 6.0

Why watch this? A perfect follow-up to Sleepless in Madrid for fans of Drama & Comedy & Romance. It captures a similar light-hearted atmosphere.

Just as Amelia thinks she's over her anxiety and insecurity, her best friend announces her engagement, bringing her anxiety and insecurity right back....

#3
He Said, She Said

He Said, She Said

1991‱★ 5.8

Why watch this? A perfect follow-up to Sleepless in Madrid for fans of Drama & Comedy & Romance. It captures a similar light-hearted atmosphere.

Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing...

#4
Broken English

Broken English

2007‱★ 5.9

Why watch this? A perfect follow-up to Sleepless in Madrid for fans of Drama & Comedy & Romance. It captures a similar light-hearted atmosphere.

Nora Wilder is freaking out. Everyone around her is either in a relationship, married, or has children, while she's in her thirties, alone with job she's outgrown and a mother who ...

#5
XX/XY

XX/XY

2002‱★ 5.8

Why watch this? A perfect follow-up to Sleepless in Madrid for fans of Drama & Comedy & Romance. It captures a similar light-hearted atmosphere.

Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later....

#6
The Olive Tree

The Olive Tree

2016‱★ 6.7

Why watch this? A perfect follow-up to Sleepless in Madrid for fans of Drama & Comedy. It captures a similar light-hearted atmosphere.

Alma’s family has been producing quality olive oil in the Baix Maestrat area of Spain’s Castellón for generations. Yet changing pressures in the industry have made their traditiona...

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