Dynamic Watchlist Hub: Apr 18, 2026

10 Best Movies Like With Love, Lilly

If you loved With Love, Lilly, 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 With Love, Lilly.

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#1
Love & Sex

Love & Sex

2000★ 6.1

Why watch this? A perfect follow-up to With Love, Lilly for fans of Comedy & Drama & 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 With Love, Lilly for fans of Comedy & Drama & 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
About Love

About Love

2015★ 5.9

Why watch this? A perfect follow-up to With Love, Lilly for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

What is love? The heroes of the film try to answer this question. A series of the most different characters and their stories are woven together. Small stories about various things...

#4
He Said, She Said

He Said, She Said

1991★ 5.8

Why watch this? A perfect follow-up to With Love, Lilly for fans of Comedy & Drama & 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...

#5
Love Don't Co$t a Thing

Love Don't Co$t a Thing

2003★ 7.6

Why watch this? A perfect follow-up to With Love, Lilly for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool....

#6
Peace, Love & Misunderstanding

Peace, Love & Misunderstanding

2011★ 5.8

Why watch this? A perfect follow-up to With Love, Lilly for fans of Comedy & Drama & Romance. It captures a similar light-hearted atmosphere.

A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce....

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