Dynamic Watchlist Hub: Jan 19, 2026

10 Best Movies Like Definitely, Maybe

If you loved Definitely, Maybe, 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 Definitely, Maybe.

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#1
Juno

Juno

2007★ 7.1

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

Faced with an unplanned pregnancy, sixteen year old high-schooler, Juno MacGuff, makes an unusual decision regarding her unborn child....

#2
Just Friends

Just Friends

2005★ 6.2

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

While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush whom he was best friends with – a woman whose rejection of him turned him into...

#3
Deewane Huye Paagal

Deewane Huye Paagal

2005★ 5.0

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

A man embarks on journey to find his love in Dubai, only to learn she has different suitors and admirers....

#4
My Best Friend's Wedding

My Best Friend's Wedding

1997★ 6.6

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

When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Mi...

#5
Some Kind of Wonderful

Some Kind of Wonderful

1987★ 6.9

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

Keith Nelson, an artsy high school outcast, tries to land a date with popular girl Amanda Jones with some help from his tomboy best friend, Watts. However, Watts realizes she likes...

#6
Confessions of a Shopaholic

Confessions of a Shopaholic

2009★ 6.5

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

In the glamorous world of New York City, Rebecca Bloomwood is a fun-loving girl who is really good at shopping – a little too good, perhaps. She dreams of working for her favorite ...